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Dembo, António
CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine–Chalcone Hybrids
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A series of novel triazole-tethered ferrocenoylamino-substituted cinchona–chalcone hybrids along with two representative benzoylamino-substituted reference compounds were prepared by three methods of CuAAC chemistry. In line with the limited success or complete failure of attempted conversions with low catalyst loadings, by means of DFT modeling studies, we demonstrated that a substantial part of the Cu(I) ions can be chelated and thus trapped in the aroylamino-substituted cinchona fragment and all of the accessible coordinating sites of the chalcone residues. Accordingly, increased amounts of catalysts were used to achieve acceptable yields; however, the cycloadditions with para-azidochalcones were accompanied by partial or complete aldehyde-forming hydrolytic fission of the enone C=C bond in a substituent-, solvent- and copper load-dependent manner. The experienced hydrolytic stability of the hybrids obtained by cycloadditions with ortho-azidochalcones was interpreted in terms of relative energetics, DFT reactivity indices and MO analysis of simplified models of two isomer copper–enone complexes. The novel hybrids were evaluated on HeLa, MDA-MB-231 and A2780 cell lines and showed substantial activity at low-to-submicromolar concentrations. An organometallic model carrying 3,4,5-trimethoxyphenyl residue in the enone part with a para-disubstituted benzene ring in the central skeletal region was identified as the most potent antiproliferative lead, characterized by submicromolar IC50 values measured on the three investigated cells. The biological assays also disclosed that this ferrocenoylamino-containing lead compound displays a ca. two- to five-fold more substantial antiproliferative effect than its benzoylamino-substituted counterpart.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" > Dembo, António </span> <span class="author-type"> </span> ; <span class="author-name" > Ferenczi, Etelka </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10052855"> <a href="/gui2/?type=authors&mode=browse&sel=10052855" target="_blank">Jernei, Tamás ✉</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10029753"> <a href="/gui2/?type=authors&mode=browse&sel=10029753" target="_blank">Bor, Andrea</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10048235"> <a href="/gui2/?type=authors&mode=browse&sel=10048235" target="_blank">Schelz, Zsuzsanna</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001074"> <a href="/gui2/?type=authors&mode=browse&sel=10001074" target="_blank">Zupkó, István</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10014762"> <a href="/gui2/?type=authors&mode=browse&sel=10014762" target="_blank">Varga, Szilárd</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;34499406" mtid="34499406" target="_blank">CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine–Chalcone Hybrids</a></div> <div class="pub-info"> <span class="journal-title">MOLECULES</span> <span class="journal-volume">29</span> : <span class="journal-issue">2</span> <span class="page"> Paper: 375 , 23 p. </span> <span class="year">(2024)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/molecules29020375" target="_blank" href="https://doi.org/10.3390/molecules29020375"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="001151390100001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/001151390100001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85183257921" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85183257921"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="38257289" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=38257289&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.mdpi.com/1420-3049/29/2/375" target="_blank" href="https://www.mdpi.com/1420-3049/29/2/375"> Egyéb URL </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="29574" target="_blank" href="http://publicatio.bibl.u-szeged.hu/29574"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:34499406 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" >Dembo António </span> ; <span class="author-name" >Ferenczi Etelka </span> ; <span class="author-name" mtid="10052855"><a href="/gui2/?type=authors&mode=browse&sel=10052855" target="_blank">Jernei Tamás ✉ (<span class="authorship-author-name">Jernei Tamás</span> <span class="authorAux-mtmt"> Szerves és Fémorganikus Kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" mtid="10029753"><a href="/gui2/?type=authors&mode=browse&sel=10029753" target="_blank">Bor Andrea (<span class="authorship-author-name">Bor Andrea</span> <span class="authorAux-mtmt"> Klinikai gyógyszerészet</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerhatástani és Biofarmáciai Intézet</span> ; <span class="author-name" mtid="10048235"><a href="/gui2/?type=authors&mode=browse&sel=10048235" target="_blank">Schelz Zsuzsanna (<span class="authorship-author-name">Schelz Zsuzsanna</span> <span class="authorAux-mtmt"> Gyógyszerésztudomány</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerhatástani és Biofarmáciai Intézet</span> ; <span class="author-name" mtid="10001074"><a href="/gui2/?type=authors&mode=browse&sel=10001074" target="_blank">Zupkó István (<span class="authorship-author-name">Zupkó István</span> <span class="authorAux-mtmt"> Farmakológia</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerhatástani és Biofarmáciai Intézet</span> ; <span class="author-name" mtid="10014762"><a href="/gui2/?type=authors&mode=browse&sel=10014762" target="_blank">Varga Szilárd (<span class="authorship-author-name">Varga Szilárd</span> <span class="authorAux-mtmt"> Szintetikus Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="HUN-REN Természettudományi Kutatóközpont">HRN TTK</span>/<span title="Szerves Kémiai Intézet">SZKI</span>/Organokatalízis Kutatócsoport (Lendület FLP Kutatócsoport); <span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai Antal ✉ (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;34499406" target="_blank">CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine–Chalcone Hybrids</a></div> <div> <span class="journal-title">MOLECULES</span> <span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a>)</span>: <span class="journal-volume">29</span> <span class="journal-issue">2</span> <span class="page"> Paper 375. 23 p. </span> <span class="year">(2024)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/molecules29020375" target="_blank" href="https://doi.org/10.3390/molecules29020375"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="001151390100001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/001151390100001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85183257921" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85183257921"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="38257289" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=38257289&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.mdpi.com/1420-3049/29/2/375" target="_blank" href="https://www.mdpi.com/1420-3049/29/2/375"> Egyéb URL </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="29574" target="_blank" href="http://publicatio.bibl.u-szeged.hu/29574"> SZTE Publicatio </a> </span> </span> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;34499406&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 7 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 34499406</span> | <span class="status-data status-VALIDATED"> Egyeztetett </span> Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="lastModified">Utolsó módosítás: 2024.02.16. 12:03 Szalai Fruzsina (SZTE admin5) </div> </div></div>
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In a search for novel therapeutic options for head and neck squamous cell carcinomas (HNSCCs) generally treated with limited therapeutic success, we synthesized a series of novel erlotinib–chalcone molecular hybrids with 1,2,3-triazole and alkyne linkers and evaluated them for their anticancer activity on Fadu, Detroit 562 and SCC-25 HNSCC cell lines. Time- and dose-dependent cell viability measurements disclosed a significantly increased efficiency of the hybrids compared to the 1:1 combination of erlotinib and a reference chalcone. The clonogenic assay demonstrated that hybrids eradicate HNSCC cells in low micromolar concentrations. Experiments focusing on potential molecular targets indicate that the hybrids trigger the anticancer effect by a complementary mechanism of action that is independent of the canonical targets of their molecular fragments. Confocal microscopic imaging and real-time apoptosis/necrosis detection assay pointed to slightly different cell death mechanisms induced by the most prominent triazole- and alkyne-tethered hybrids (6a and 13, respectively). While 6a featured the lowest IC50 values on each of the three HNSCC cell lines, in Detroit 562 cells, this hybrid induced necrosis more markedly compared to 13. The therapeutic potential indicated by the observed anticancer efficacy of our selected hybrid molecules validates the concept of development and justifies further investigation to reveal the underlying mechanism of action.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10047778"> <a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Murányi, József</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10093972"> <a href="/gui2/?type=authors&mode=browse&sel=10093972" target="_blank">Duró, Cintia</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10059086"> <a href="/gui2/?type=authors&mode=browse&sel=10059086" target="_blank">Gurbi, Bianka</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10082532"> <a href="/gui2/?type=authors&mode=browse&sel=10082532" target="_blank">Móra, István</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10040840"> <a href="/gui2/?type=authors&mode=browse&sel=10040840" target="_blank">Varga, Attila</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10076057"> <a href="/gui2/?type=authors&mode=browse&sel=10076057" target="_blank">Németh, Krisztina</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10049429"> <a href="/gui2/?type=authors&mode=browse&sel=10049429" target="_blank">Simon, József</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10000786"> <a href="/gui2/?type=authors&mode=browse&sel=10000786" target="_blank">Csala, Miklós ✉</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;33635331" mtid="33635331" target="_blank">Novel Erlotinib–Chalcone Hybrids Diminish Resistance in Head and Neck Cancer by Inducing Multiple Cell Death Mechanisms</a></div> <div class="pub-info"> <span class="journal-title">INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES</span> <span class="journal-volume">24</span> : <span class="journal-issue">4</span> <span class="page"> Paper: 3456 , 18 p. </span> <span class="year">(2023)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/ijms24043456" target="_blank" href="https://doi.org/10.3390/ijms24043456"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000938691600001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000938691600001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85149015206" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85149015206"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="36834866" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=36834866&dopt=Abstract"> PubMed </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:33635331 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" mtid="10047778"><a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Murányi József (<span class="authorship-author-name">Murányi József</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10093972"><a href="/gui2/?type=authors&mode=browse&sel=10093972" target="_blank">Duró Cintia (<span class="authorship-author-name">Jernei-Duró Cintia</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" mtid="10059086"><a href="/gui2/?type=authors&mode=browse&sel=10059086" target="_blank">Gurbi Bianka (<span class="authorship-author-name">Gurbi Bianka</span> <span class="authorAux-mtmt"> célzott daganatterápia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10082532"><a href="/gui2/?type=authors&mode=browse&sel=10082532" target="_blank">Móra István (<span class="authorship-author-name">Móra István András</span> <span class="authorAux-mtmt"> Biomérnök</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10040840"><a href="/gui2/?type=authors&mode=browse&sel=10040840" target="_blank">Varga Attila (<span class="authorship-author-name">Varga Attila</span> <span class="authorAux-mtmt"> molekuláris biológia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10076057"><a href="/gui2/?type=authors&mode=browse&sel=10076057" target="_blank">Németh Krisztina (<span class="authorship-author-name">Németh Krisztina</span> <span class="authorAux-mtmt"> Tömegspektrometria</span>) </a> </span> ; <span class="author-name" mtid="10049429"><a href="/gui2/?type=authors&mode=browse&sel=10049429" target="_blank">Simon József (<span class="authorship-author-name">Simon József</span> <span class="authorAux-mtmt"> 2D korreláció analízis</span>) </a> </span> <span class="author-affil"><span title="Pannon Egyetem">PE</span>/<span title="Mérnöki Kar">MK</span>/Természettudományi Központ</span> ; <span class="author-name" mtid="10000786"><a href="/gui2/?type=authors&mode=browse&sel=10000786" target="_blank">Csala Miklós ✉ (<span class="authorship-author-name">Csala Miklós</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai Antal ✉ (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;33635331" target="_blank">Novel Erlotinib–Chalcone Hybrids Diminish Resistance in Head and Neck Cancer by Inducing Multiple Cell Death Mechanisms</a></div> <div> <span class="journal-title">INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES</span> <span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/1661-6596">1661-6596</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1422-0067">1422-0067</a>)</span>: <span class="journal-volume">24</span> <span class="journal-issue">4</span> <span class="page"> Paper 3456. 18 p. </span> <span class="year">(2023)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/ijms24043456" target="_blank" href="https://doi.org/10.3390/ijms24043456"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000938691600001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000938691600001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85149015206" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85149015206"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="36834866" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=36834866&dopt=Abstract"> PubMed </a> </span> </span> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;33635331&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 4 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 33635331</span> | <span class="status-data status-VALIDATED"> Egyeztetett </span> Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="funder"> (K-129037) Támogató: OTKA, (NVKP_16-1-2016-0036), (2018-1.2.1-NKP-2018-00005) Támogató: NKFIH, (K124813), (2020-4.1.1.-TKP2020), (TKP2021-EGA-24) </div> <div class="lastModified">Utolsó módosítás: 2024.02.09. 20:14 Jernei-Duró Cintia (Szerves kémia) </div> </div></div>
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Laboratory of Structural Chemistry and Biology, Institute of Chemistry, Eötvös Loránd University, Pázmány P. Stny. 1/A, Budapest, 1117, Hungary
György Hevesy Doctoral School of Chemistry, Eötvös Loránd University, Budapest, Hungary
ELKH-ELTE Protein Modeling Research Group, Pázmány P. Stny. 1/A, Budapest, 1117, Hungary
Organic Chemistry Department, Eötvös Loránd University, Pázmány P. Stny. 1/A, Budapest, 1117, Hungary
Export Date: 2 October 2023
CODEN: AACIE
Correspondence Address: Perczel, A.; Laboratory of Structural Chemistry and Biology, Pázmány P. Stny. 1/A, Hungary; email: perczel.andras@ttk.elte.hu
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The synthesis of d- glucosamine-1-carboxylic acid based β-sugar amino acids (β-SAAs) is typically performed in nine consecutive steps via an inefficient OAc → Br → CN conversion protocol with low overall yield. Here, we present the improved and more efficient synthesis of both Fmoc-GlcAPC-OH and Fmoc-GlcAPC(Ac)-OH, β-SAAs consisting of only 4–5 synthetic steps. Their active ester and amide bond formation with glycine methyl ester (H-Gly-OMe) was completed and monitored by 1 H NMR. The stability of the pyranoid OHs protecting the acetyl groups was investigated under three different Fmoc cleavage conditions and was found to be satisfactory even at high piperidine concentration (e.g. 40%). We designed a SPPS protocol using Fmoc-GlcAPC(Ac)-OH to produce model peptides Gly-β-SAA-Gly as well as Gly-β-SAA-β-SAA-Gly with high coupling efficiency. The products were deacetylated using the Zemplén method, which allows the hydrophilicity of a building block and/or chimera to be fine-tuned, even after the polypeptide chain has already been synthesized.
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ELKH-ELTE Fehérjemodellező Kutatócsoport (ELTE / TTK / KI); Hevesy György Kémia Doktori Iskola (ELTE / TTK); Szerkezeti Kémiai és Biológiai Laboratórium (Sz... (ELTE / TTK / KI); Szerves Kémiai Tanszék (ELTE / TTK / KI)
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10073622"> <a href="/gui2/?type=authors&mode=browse&sel=10073622" target="_blank">Varga, István</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10055786"> <a href="/gui2/?type=authors&mode=browse&sel=10055786" target="_blank">Goldschmidt Gőz, Viktória</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002875"> <a href="/gui2/?type=authors&mode=browse&sel=10002875" target="_blank">Pintér, István</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1062306"> <a href="/gui2/?type=authors&mode=browse&sel=1062306" target="_blank">Perczel, András ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;34036752" mtid="34036752" target="_blank">Acetyl group for proper protection of β-sugar-amino acids used in SPPS</a></div> <div class="pub-info"> <span class="journal-title">AMINO ACIDS</span> <span class="journal-volume">55</span> <span class="page"> pp. 969-979. , 11 p. </span> <span class="year">(2023)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.1007/s00726-023-03278-1" target="_blank" href="https://doi.org/10.1007/s00726-023-03278-1"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="001011705400001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/001011705400001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85162249774" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85162249774"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="37340192" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=37340192&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://link.springer.com/10.1007/s00726-023-03278-1" target="_blank" href="https://link.springer.com/10.1007/s00726-023-03278-1"> Egyéb URL </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:34036752 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 1</span> | Független: 1 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 1 | WoS/Scopus jelölt: 1 | DOI jelölt: 1 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;34036752" target="_blank">Acetyl group for proper protection of β-sugar-amino acids used in SPPS</a></div> <div> <span class="journal-title">AMINO ACIDS</span>
<span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/0939-4451">0939-4451</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1438-2199">1438-2199</a>)</span>:
<span class="journal-volume">55</span>
<span class="page">
pp 969-979
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<span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 1</span>
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| <span class="status-data status-VALIDATED"> Egyeztetett
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Forrás Idéző
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<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: Laboratory of Structural Chemistry and Biology, Institute of Chemistry, Eötvös Loránd University, Pázmány P. Stny. 1/A, Budapest, 1117, Hungary
György Hevesy Doctoral School of Chemistry, Eötvös Loránd University, Budapest, Hungary
ELKH-ELTE Protein Modeling Research Group, Pázmány P. Stny. 1/A, Budapest, 1117, Hungary
Orga...</pre>
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" > Alaoui, Nour-Eddine El </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10088081"> <a href="/gui2/?type=authors&mode=browse&sel=10088081" target="_blank">Boulhaoua, Mohammed</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10072860"> <a href="/gui2/?type=authors&mode=browse&sel=10072860" target="_blank">Hutai, Dániel</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002260"> <a href="/gui2/?type=authors&mode=browse&sel=10002260" target="_blank">Oláh-Szabó, Rita</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002049"> <a href="/gui2/?type=authors&mode=browse&sel=10002049" target="_blank">Bősze, Szilvia</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1355751"> <a href="/gui2/?type=authors&mode=browse&sel=1355751" target="_blank">Hudecz, Ferenc<sup>**</sup></a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;32847481" mtid="32847481" target="_blank">Synthetic and DFT Modeling Studies on Suzuki–Miyaura Reactions of 4,5-Dibromo-2-methylpyridazin-3(2H)-one with Ferrocene Boronates, Accompanied by Hydrodebromination and a Novel Bridge-Forming Annulation In Vitro Cytotoxic Activity of the Ferrocenyl–Pyridazinone Products</a></div> <div class="pub-info"> <span class="journal-title">CATALYSTS</span> <span class="journal-volume">12</span> : <span class="journal-issue">6</span> <span class="page"> Paper: 578 , 21 p. </span> <span class="year">(2022)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/catal12060578" target="_blank" href="https://doi.org/10.3390/catal12060578"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000816068200001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000816068200001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85131623441" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85131623441"> Scopus </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:32847481 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" >Alaoui Nour-Eddine El </span> ; 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<span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai Antal ✉ (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32847481" target="_blank">Synthetic and DFT Modeling Studies on Suzuki–Miyaura Reactions of 4,5-Dibromo-2-methylpyridazin-3(2H)-one with Ferrocene Boronates, Accompanied by Hydrodebromination and a Novel Bridge-Forming Annulation In Vitro Cytotoxic Activity of the Ferrocenyl–Pyridazinone Products</a></div> <div> <span class="journal-title">CATALYSTS</span> <span class="journal-issn">( <a target="_blank" href="https://portal.issn.org/resource/ISSN/2073-4344">2073-4344</a>)</span>: <span class="journal-volume">12</span> <span class="journal-issue">6</span> <span class="page"> Paper 578. 21 p. </span> <span class="year">(2022)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/catal12060578" target="_blank" href="https://doi.org/10.3390/catal12060578"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000816068200001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000816068200001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85131623441" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85131623441"> Scopus </a> </span> </span> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;32847481&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 11 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 32847481</span> | <span class="status-data status-VALIDATED"> Egyeztetett </span> Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="lastModified">Utolsó módosítás: 2024.02.06. 12:57 Sághi-Keszthelyi Anna (SE_KK_Admin5_SKA, admin) </div> </div></div>
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10078497"> <a href="/gui2/?type=authors&mode=browse&sel=10078497" target="_blank">Czuczi, Tamás</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10047778"> <a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Murányi, József</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10078434"> <a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">Bárány, Péter</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10082532"> <a href="/gui2/?type=authors&mode=browse&sel=10082532" target="_blank">Móra, István</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10062533"> <a href="/gui2/?type=authors&mode=browse&sel=10062533" target="_blank">Borbély, Adina</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10000786"> <a href="/gui2/?type=authors&mode=browse&sel=10000786" target="_blank">Csala, Miklós</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;32782717" mtid="32782717" target="_blank">Synthesis and Antiproliferative Activity of Novel Imipridone–Ferrocene Hybrids with Triazole and Alkyne Linkers</a></div> <div class="pub-info"> <span class="journal-title">PHARMACEUTICALS</span> <span class="journal-volume">15</span> : <span class="journal-issue">4</span> <span class="page"> Paper: 468 , 19 p. </span> <span class="year">(2022)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/ph15040468" target="_blank" href="https://doi.org/10.3390/ph15040468"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000787448800001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000787448800001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85128994841" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85128994841"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="35455465" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=35455465&dopt=Abstract"> PubMed </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:32782717 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 3</span> | Független: 3 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | Scopus jelölt: 3 | WoS/Scopus jelölt: 3 | DOI jelölt: 3 </div> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" mtid="10078497"><a href="/gui2/?type=authors&mode=browse&sel=10078497" target="_blank">Czuczi Tamás (<span class="authorship-author-name">Czuczi Tamás</span> <span class="authorAux-mtmt"> Kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" mtid="10047778"><a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Murányi József (<span class="authorship-author-name">Murányi József</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/<span title="Molekuláris Biológiai Tanszék">MBT</span>/MTA-SE Patobiokémiai Kutatócsoport</span> ; <span class="author-name" mtid="10078434"><a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">Bárány Péter (<span class="authorship-author-name">Bárány Péter Tibor</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" mtid="10082532"><a href="/gui2/?type=authors&mode=browse&sel=10082532" target="_blank">Móra István (<span class="authorship-author-name">Móra István András</span> <span class="authorAux-mtmt"> Biomérnök</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/<span title="Molekuláris Biológiai Tanszék">MBT</span>/MTA-SE Patobiokémiai Kutatócsoport</span> ; <span class="author-name" mtid="10062533"><a href="/gui2/?type=authors&mode=browse&sel=10062533" target="_blank">Borbély Adina (<span class="authorship-author-name">Borbély Adina Noémi</span> <span class="authorAux-mtmt"> Kémia, vegyész</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/MTA-ELTE Lendület Ionmobilitás-tömegspektrometria Kutatócsoport</span> ; <span class="author-name" mtid="10000786"><a href="/gui2/?type=authors&mode=browse&sel=10000786" target="_blank">Csala Miklós (<span class="authorship-author-name">Csala Miklós</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> <span class="author-affil"><span title="MTA Támogatott Kutatócsoportok">MTA TKI</span>/MTA-SE Endoplazmatikus Retikulum Kutatócsoport (2007-től beolvadt az SE16-ba); <span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/Molekuláris Biológiai Tanszék</span> ; <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai Antal ✉ (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32782717" target="_blank">Synthesis and Antiproliferative Activity of Novel Imipridone–Ferrocene Hybrids with Triazole and Alkyne Linkers</a></div> <div> <span class="journal-title">PHARMACEUTICALS</span> <span class="journal-issn">( <a target="_blank" href="https://portal.issn.org/resource/ISSN/1424-8247">1424-8247</a>)</span>: <span class="journal-volume">15</span> <span class="journal-issue">4</span> <span class="page"> Paper 468. 19 p. </span> <span class="year">(2022)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/ph15040468" target="_blank" href="https://doi.org/10.3390/ph15040468"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000787448800001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000787448800001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85128994841" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85128994841"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="35455465" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=35455465&dopt=Abstract"> PubMed </a> </span> </span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 3</span> | Független: 3 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | Scopus jelölt: 3 | WoS/Scopus jelölt: 3 | DOI jelölt: 3 </div> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;32782717&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 1 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 32782717</span> | <span class="status-data status-VALIDATED"> Egyeztetett </span> Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="funder"> (K-129037) Támogató: OTKA, (NVKP_16-1-2016-0036), (NKP-2018-1.2.1-NKP-2018-00005), (SzintPlusz_1117), (K 124813) Támogató: NKFIH, (2020-4.1.1-TKP2020) Támogató: NKFIH, Thematic Institutional Excellence Programme(TKP2021-EGA-24) Támogató: Emberi Erőforrások Minisztériuma, (VEKOP-2.3.3-15-2017-00020) Támogató: EU </div> <div class="lastModified">Utolsó módosítás: 2023.01.20. 12:41 Lövei Anett (ELTE TTK 5-ös admin) </div> </div></div>
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Synthesis of novel imipridone derivatives and their evaluation for their anticancer activity.
WO2022029459A1
91pp.
91
2022
The present invention relates to compds. of formula (I) (I) or pharmaceutically acceptable salts, and stereoisomers thereof, including enantiomers, racemic mixts., mixts. of enantiomers, or combinations thereof, which are applicable for use in treating cancer diseases. The present invention further relates to a pharmaceutical compn. comprising the above compds. [on SciFinder(R)]
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<div class="Patent Publication short-list"> <div class="authors"> <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csampai, Antal</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10078434"> <a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">Barany, Peter</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Czuczi, Tamas </span> <span class="author-type"> </span> ; <span class="author-name" > Kovacs, Imre </span> <span class="author-type"> </span> ; <span class="author-name" > Adamis, Balint </span> <span class="author-type"> </span> ; <span class="author-name" > Nemeth, Zsofia </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10047778"> <a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Muranyi, Jozsef</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Olahne, Szabo Rita </span> <span class="author-type"> </span> ; <span class="author-name" > Bosze, Szilvia </span> <span class="author-type"> </span> ; <span class="author-name" > Mezo, Gabor </span> <span class="author-type"> </span> et al. </div > <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32683354" mtid="32683354" target="_blank">Synthesis of novel imipridone derivatives and their evaluation for their anticancer activity.<span class="subTitle">: WO2022029459A1</span></a></div> <div class="pub-info"> , <span class="submissionNumber">Benyújtás száma: WO2005108388A1</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.danubia.com/ipmall/synthesis-of-novel-imipridone-derivatives-and-their-evaluation-for-their-anticancer-activity/" target="_blank" href="https://www.danubia.com/ipmall/synthesis-of-novel-imipridone-derivatives-and-their-evaluation-for-their-anticancer-activity/"> Egyéb URL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022029459&_cid=P21-LA9III-93871-1" target="_blank" href="https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022029459&_cid=P21-LA9III-93871-1"> Egyéb URL </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:32683354 </span> <span class="status-holder"><span class="status-data status-ADMIN_APPROVED"> Admin láttamozott </span></span> <span class="pub-core">Forrás </span> <span class="pub-type">Oltalmi formák (Nemzetközi szabadalom ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="Patent Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <div class="autype autype0"> <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csampai Antal (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> ; <span class="author-name" mtid="10078434"><a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">Barany Peter (<span class="authorship-author-name">Bárány Péter Tibor</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> ; <span class="author-name" >Czuczi Tamas </span> ; <span class="author-name" >Kovacs Imre </span> ; <span class="author-name" >Adamis Balint </span> ; <span class="author-name" >Nemeth Zsofia </span> ; <span class="author-name" mtid="10047778"><a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">Muranyi Jozsef (<span class="authorship-author-name">Murányi József</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/<span title="Biokémiai és Molekuláris Biológiai Intézet">BMBI</span>/<span title="Molekuláris Biológiai Tanszék">MBT</span>/MTA-SE Patobiokémiai Kutatócsoport</span> ; 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<span class="author-name" mtid="10062490"><a href="/gui2/?type=authors&mode=browse&sel=10062490" target="_blank">Takacs Angela (<span class="authorship-author-name">Takács Angéla</span> <span class="authorAux-mtmt"> gyógyszerésztudományok</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/Genetikai, Sejt- és Immunbiológiai Intézet</span> ; <span class="author-name" mtid="10027592"><a href="/gui2/?type=authors&mode=browse&sel=10027592" target="_blank">Lang Orsolya (<span class="authorship-author-name">Láng Orsolya</span> <span class="authorAux-mtmt"> sejtbiológia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Általános Orvostudományi Kar">AOK</span>/<span title="Intézet">I</span>/Genetikai, Sejt- és Immunbiológiai Intézet</span> ; <span class="author-name" >Mezo Diana </span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32683354" target="_blank">Synthesis of novel imipridone derivatives and their evaluation for their anticancer activity. : WO2022029459A1.</a></div> <span class="patent-submission"> Benyújtás száma: WO2005108388A1 | </span> <div class="publishedYear">Közzététel éve: (2022)</div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.danubia.com/ipmall/synthesis-of-novel-imipridone-derivatives-and-their-evaluation-for-their-anticancer-activity/" target="_blank" href="https://www.danubia.com/ipmall/synthesis-of-novel-imipridone-derivatives-and-their-evaluation-for-their-anticancer-activity/"> Egyéb URL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022029459&_cid=P21-LA9III-93871-1" target="_blank" href="https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022029459&_cid=P21-LA9III-93871-1"> Egyéb URL </a> </span> </span> <div class="mtid"><span class="long-pub-mtid">Közlemény: 32683354</span> | <span class="status-data status-ADMIN_APPROVED"> Admin láttamozott </span> Forrás | <span class="type-subtype">Oltalmi formák ( Nemzetközi szabadalom ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">RIS-Egyéb</span> </div> <div class="notDuplums"><a target="_blank" href="/api/publication/32683354/notduplums">1 Nem duplumnak jelölés</a> </div> <div class="lastModified">Utolsó módosítás: 2023.12.11. 15:43 Csajbók Edit (SE_KK_Admin5_CSE, admin) </div> </div></div>
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<span class="author-name" >Fodor Kinga Judit </span> ; <span class="author-name" >Hutai Dániel Gábor </span> ; <span class="author-name" >Jernei Tamás </span> ; <span class="author-name" >Sulyok-Eiler Máté </span> ; <span class="author-name" >Harmat Veronika </span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;33053795" target="_blank">Részlegesen telített polikondenzált indolszármazékok szintézise és szerkezetanalízise, a diasztereoszelektív reakciólépések mechanizmusának elméleti modellezése.</a></div> <div class="InBook"><div class="chapter-in">In:</div> <div class="authors"> <div class="autype autype-1"> <span class="author-name" >Magyar Kémikusok Egyesülete </span> (szerk.) </div> </div> <div class="booktitle"><a href="/gui2/?mode=browse¶ms=publication;33053789" target="_blank">Vegyészkonferencia 2022 </a></div> <div class="conference"> Konferencia helye, ideje: <span class="location">Eger, Magyarország <span class="conference-date">2022.06.15. - 2022.06.17.</span> </div> <span class="publishedAt">Budapest: <span class="publishers">Magyar Kémikusok Egyesülete (MKE)</span>, <span class="page"> Paper O-15. </span> <span class="year">(2022)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Magyar | </span> <span class="identifiers"> </span> <span class="bookchapter-ids">Befoglaló link(ek):</span> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <span class="isbnOrIssn"> ISBN: </span> <a style="color:black" title="9786156018113" target="_blank" href="https://www.worldcat.org/search?q=isbn%3A9786156018113"> 9786156018113 </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://vegykonf2022.mke.org.hu/images/documents/vegyeszkonferencia-2022-osszefoglalo-ekonyv.pdf" target="_blank" href="https://vegykonf2022.mke.org.hu/images/documents/vegyeszkonferencia-2022-osszefoglalo-ekonyv.pdf"> Teljes dokumentum </a> </span> </span> <div class="mtid"><span class="long-pub-mtid">Közlemény: 33053795</span> | <span class="status-data status-ADMIN_APPROVED"> Admin láttamozott </span> <span class="long-book-mtid">Befoglaló: 33053789</span> Forrás | <span class="type-subtype">Könyvrészlet ( Absztrakt / Kivonat ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="lastModified">Utolsó módosítás: 2023.02.08. 11:41 Lövei Anett (ELTE TTK 5-ös admin) </div> </div> </div>
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<div class="Patent Publication short-list"> <div class="authors"> <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">CSÁMPAI, ANTAL</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10078434"> <a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">BÁRÁNY, PÉTER</a> </span> <span class="author-type"> </span> ; <span class="author-name" > CZUCZI, TAMÁS </span> <span class="author-type"> </span> ; <span class="author-name" > KOVÁCS, IMRE </span> <span class="author-type"> </span> ; <span class="author-name" > ADAMIS, BÁLINT </span> <span class="author-type"> </span> ; <span class="author-name" > NÉMETH, ZSÓFIA </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10047778"> <a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">MURÁNYI, JÓZSEF</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002260"> <a href="/gui2/?type=authors&mode=browse&sel=10002260" target="_blank">OLÁHNÉ, SZABÓ RITA</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002049"> <a href="/gui2/?type=authors&mode=browse&sel=10002049" target="_blank">BŐSZE, SZILVIA</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001614"> <a href="/gui2/?type=authors&mode=browse&sel=10001614" target="_blank">MEZŐ, GÁBOR</a> </span> <span class="author-type"> </span> et al. </div > <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32787939" mtid="32787939" target="_blank">SYNTHESIS OF NOVEL IMIPRIDONE DERIVATIVES AND THEIR EVALUATION FOR THEIR ANTICANCER ACTIVITY</a></div> <div class="pub-info"> <span class="patentnumber">WO2022029459A1</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="https://patents.google.com/patent/WO2022029459A1" target="_blank" href="https://patents.google.com/patent/WO2022029459A1"> Teljes dokumentum </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:32787939 </span> <span class="status-holder"><span class="status-data status-APPROVED"> Nyilvános </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Oltalmi formák (Nemzetközi szabadalom ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="Patent Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">CSÁMPAI ANTAL (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szervetlen Kémiai Tanszék</span> ; <span class="author-name" mtid="10078434"><a href="/gui2/?type=authors&mode=browse&sel=10078434" target="_blank">BÁRÁNY PÉTER (<span class="authorship-author-name">Bárány Péter Tibor</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> ; <span class="author-name" >CZUCZI TAMÁS </span> ; <span class="author-name" >KOVÁCS IMRE </span> ; <span class="author-name" >ADAMIS BÁLINT </span> ; <span class="author-name" >NÉMETH ZSÓFIA </span> ; <span class="author-name" mtid="10047778"><a href="/gui2/?type=authors&mode=browse&sel=10047778" target="_blank">MURÁNYI JÓZSEF (<span class="authorship-author-name">Murányi József</span> <span class="authorAux-mtmt"> Biokémia</span>) </a> </span> ; <span class="author-name" mtid="10002260"><a href="/gui2/?type=authors&mode=browse&sel=10002260" target="_blank">OLÁHNÉ SZABÓ RITA (<span class="authorship-author-name">Szabó Rita (Oláhné)</span> <span class="authorAux-mtmt"> Sejtbiológia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/MTA-ELTE Peptidkémiai Kutatócsoport</span> ; <span class="author-name" mtid="10002049"><a href="/gui2/?type=authors&mode=browse&sel=10002049" target="_blank">BŐSZE SZILVIA (<span class="authorship-author-name">Bősze Szilvia</span> <span class="authorAux-mtmt"> Peptidkémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/MTA-ELTE Peptidkémiai Kutatócsoport</span> ; <span class="author-name" mtid="10001614"><a href="/gui2/?type=authors&mode=browse&sel=10001614" target="_blank">MEZŐ GÁBOR (<span class="authorship-author-name">Mező Gábor</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/MTA-ELTE Peptidkémiai Kutatócsoport; <span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> ; <span class="author-name" >KŐHIDAI LÁSZLÓ </span> ; <span class="author-name" >LAJKÓ ESZTER </span> ; <span class="author-name" >TAKÁCS ANGÉLA </span> ; <span class="author-name" >LÁNG ORSOLYA </span> ; <span class="author-name" >MEZŐ DIÁNA </span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;32787939" target="_blank">SYNTHESIS OF NOVEL IMIPRIDONE DERIVATIVES AND THEIR EVALUATION FOR THEIR ANTICANCER ACTIVITY</a></div> <div class="patentnumber">Lajstromszám: WO2022029459A1</div> <span class="patent-submission"> </span> <div class="publishedYear">Közzététel éve: (2022)</div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="https://patents.google.com/patent/WO2022029459A1" target="_blank" href="https://patents.google.com/patent/WO2022029459A1"> Teljes dokumentum </a> </span> </span> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;32787939&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 1 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 32787939</span> | <span class="status-data status-APPROVED"> Nyilvános </span> Forrás Idéző | <span class="type-subtype">Oltalmi formák ( Nemzetközi szabadalom ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="notDuplums"><a target="_blank" href="/api/publication/32787939/notduplums">1 Nem duplumnak jelölés</a> </div> <div class="lastModified">Utolsó módosítás: 2024.02.02. 10:17 Szalóky-Siki Ágnes (SE_KK_Admin5_SZSA, admin) </div> </div></div>
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Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
Department of Organic Chemistry, Eötvös Loránd University, P.O. Box 32, Budapest, H-1518, Hungary
Stereochemistry Research Group, Eötvös Loránd Research Network, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
Export Date: 3 April 2023
Correspondence Address: Szatmári, I.; Institute of Pharmaceutical Chemistry, Eötvös u. 6, Hungary; email: szatmari.istvan@szte.hu
Correspondence Address: Csámpai, A.; Department of Organic Chemistry, P.O. Box 32, Hungary; email: antal.csampai@ttk.elte.hu
Chemicals/CAS: hydroxide, 14280-30-9; morpholine, 110-91-8; methanol, 67-56-1; water, 7732-18-5; Aldehydes; Mannich Bases; Methanol; Morpholines; Naphthols; Water
Funding details: TKP-2021-EGA-32
Funding details: Hungarian Scientific Research Fund, OTKA, K-129037, K-138871
Funding text 1: The authors’ thanks are due to the Hungarian Scientific Research Foundation (OTKA No. K-138871 and OTKA No. K-129037), the Ministry of Human Capacities, Hungary grant, TKP-2021-EGA-32 and the Gedeon Richter Plc. Centenarial Foundation.
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6-Hydroxyquinoline and 3-hydroxyisoquinoline as N-containing naphthol analogues were tested in modified Mannich reactions (mMr’s). In the case of 6-hydroxyquinoline, the outcomes of the attempted Mannich reactions were strongly influenced by the amine components. Aminoalkylation of this substrate with reagents 1-naphthaldehyde and N-benzylmethylamine led to the isolation of a diol regarded as a stabilised water adduct of an ortho-quinone methide (o-QM), of which formation can be ascribed to the presence of a hydroxide ion in a relatively higher concentration generated by the bulky and basic amine component with decreased nucleophilicity. The classical Mannich base was isolated as a single product when the amine component was replaced for morpholine, featuring nucleophilicity rather than basic character under the applied reaction conditions. Starting from the isomer substrate 3-hydroxyisoquinoline, independently on the nucleophile (methanol or morpholine) besides the formation of the classical Mannich base, the nucleophilic attack at position one of the heterocyclic substrate was also observed. The DFT analysis of the acceptor molecular orbitals of the potential electrophilic components and the thermodynamics of the assumed-possible transformations demonstrated that this regioselective addition is a feasible process on the investigated heterocyclic skeleton. DFT modelling studies also suggest that besides the steric bulk, the orbital-controlled electronic properties of the aryl group, originating from the aldehyde components, have a strong influence on the ratios and the NMR-monitored interconversions of the C-1-substituted 3-hydroxyisoquinolines and the classical Mannich bases formed in multistep reaction sequences. On the basis of the DFT analysis of the thermodynamics of alternative pathways, a reaction mechanism was proposed for the rationalization of these characteristic substrate-controlled interconversions.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10073375"> <a href="/gui2/?type=authors&mode=browse&sel=10073375" target="_blank">Csuvik, Oszkár</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10055375"> <a href="/gui2/?type=authors&mode=browse&sel=10055375" target="_blank">Barta, Petra</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10013053"> <a href="/gui2/?type=authors&mode=browse&sel=10013053" target="_blank">Szatmári, István ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;33154988" mtid="33154988" target="_blank">Fine-Tuned Reactivity of N-Containing Naphthol Analogues</a></div> <div class="pub-info"> <span class="journal-title">INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES</span> <span class="journal-volume">23</span> : <span class="journal-issue">20</span> <span class="page"> Paper: 12329 , 13 p. </span> <span class="year">(2022)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/ijms232012329" target="_blank" href="https://doi.org/10.3390/ijms232012329"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000875913000001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000875913000001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85140811425" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85140811425"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="36293186" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=36293186&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.mdpi.com/1422-0067/23/20/12329" target="_blank" href="https://www.mdpi.com/1422-0067/23/20/12329"> Egyéb URL </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="25329" target="_blank" href="http://publicatio.bibl.u-szeged.hu/25329"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:33154988 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> </div> </div> </div><div class="JournalArticle Publication long-list">
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;33154988" target="_blank">Fine-Tuned Reactivity of N-Containing Naphthol Analogues</a></div> <div> <span class="journal-title">INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES</span>
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<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
Department of Organic Chemistry, Eötvös Loránd University, P.O. Box 32, Budapest, H-1518, Hungary
Stereochemistry Research Group, Eötvös Loránd Research Network, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary
Export...</pre>
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Synthesis and SAR Analysis of Novel 4-Hydroxytamoxifen Analogues Based on Their Cytotoxic Activity and Electron-Donor Character
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Utilizing McMurry reactions of 4,4′-dihydroxybenzophenone with appropriate carbonyl compounds, a series of 4-Hydroxytamoxifen analogues were synthesized. Their cytotoxic activity was evaluated in vitro on four human malignant cell lines (MCF-7, MDA-MB 231, A2058, HT-29). It was found that some of these novel Tamoxifen analogues show marked cytotoxicity in a dose-dependent manner. The relative ROS-generating capability of the synthetized analogues was evaluated by cyclic voltammetry (CV) and DFT modeling studies. The results of cell-viability assays, CV measurements and DFT calculations suggest that the cytotoxicity of the majority of the novel compounds is mainly elicited by their interactions with cellular targets including estrogen receptors rather than triggered by redox processes. However, three novel compounds could be involved in ROS-production and subsequent formation of quinone-methide preventing proliferation and disrupting the redox balance of the treated cells. Among the cell lines studied, HT-29 proved to be the most susceptible to the treatment with compounds having ROS-generating potency.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10093972"> <a href="/gui2/?type=authors&mode=browse&sel=10093972" target="_blank">Duró, Cintia</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Jernei, Tamás </span> <span class="author-type"> </span> ; <span class="author-name" > Szekeres, Krisztina J. </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001821"> <a href="/gui2/?type=authors&mode=browse&sel=10001821" target="_blank">Láng, Győző G.</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002260"> <a href="/gui2/?type=authors&mode=browse&sel=10002260" target="_blank">Oláh-Szabó, Rita</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002049"> <a href="/gui2/?type=authors&mode=browse&sel=10002049" target="_blank">Bősze, Szilvia</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10003031"> <a href="/gui2/?type=authors&mode=browse&sel=10003031" target="_blank">Szabó, Ildikó</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1355751"> <a href="/gui2/?type=authors&mode=browse&sel=1355751" target="_blank">Hudecz, Ferenc</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008627"> <a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai, Antal ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;33154738" mtid="33154738" target="_blank">Synthesis and SAR Analysis of Novel 4-Hydroxytamoxifen Analogues Based on Their Cytotoxic Activity and Electron-Donor Character</a></div> <div class="pub-info"> <span class="journal-title">MOLECULES</span> <span class="journal-volume">27</span> : <span class="journal-issue">19</span> <span class="page"> Paper: 6758 , 24 p. </span> <span class="year">(2022)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/molecules27196758" target="_blank" href="https://doi.org/10.3390/molecules27196758"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000866916400001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000866916400001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85139847578" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85139847578"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="36235291" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=36235291&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.mdpi.com/1420-3049/27/19/6758" target="_blank" href="https://www.mdpi.com/1420-3049/27/19/6758"> Egyéb URL </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:33154738 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 2</span> | Független: 2 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | WoS/Scopus jelölt: 2 | DOI jelölt: 2 </div> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" mtid="10093972"><a href="/gui2/?type=authors&mode=browse&sel=10093972" target="_blank">Duró Cintia (<span class="authorship-author-name">Jernei-Duró Cintia</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/Hevesy György Kémia Doktori Iskola</span> ; <span class="author-name" >Jernei Tamás </span> ; <span class="author-name" >Szekeres Krisztina J. </span> ; <span class="author-name" mtid="10001821"><a href="/gui2/?type=authors&mode=browse&sel=10001821" target="_blank">Láng Győző G. (<span class="authorship-author-name">Láng Győző</span> <span class="authorAux-mtmt"> Fizikai-kémia, elektrokémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Elektrokémiai és Elektroanalitikai Laboratórium (EEL)</span> ; <span class="author-name" mtid="10002260"><a href="/gui2/?type=authors&mode=browse&sel=10002260" target="_blank">Oláh-Szabó Rita (<span class="authorship-author-name">Szabó Rita (Oláhné)</span> <span class="authorAux-mtmt"> Sejtbiológia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/ELKH-ELTE Peptidkémiai Kutatócsoport</span> ; <span class="author-name" mtid="10002049"><a href="/gui2/?type=authors&mode=browse&sel=10002049" target="_blank">Bősze Szilvia (<span class="authorship-author-name">Bősze Szilvia</span> <span class="authorAux-mtmt"> Peptidkémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/ELKH-ELTE Peptidkémiai Kutatócsoport</span> ; <span class="author-name" mtid="10003031"><a href="/gui2/?type=authors&mode=browse&sel=10003031" target="_blank">Szabó Ildikó (<span class="authorship-author-name">Szabó Ildikó</span> <span class="authorAux-mtmt"> Peptidkémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/ELKH-ELTE Peptidkémiai Kutatócsoport</span> ; <span class="author-name" mtid="1355751"><a href="/gui2/?type=authors&mode=browse&sel=1355751" target="_blank">Hudecz Ferenc (<span class="authorship-author-name">Hudecz Ferenc</span> <span class="authorAux-mtmt"> Biomolekuláris kémia, immunkémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/MTA-ELTE Peptidkémiai Kutatócsoport; <span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> ; <span class="author-name" mtid="10008627"><a href="/gui2/?type=authors&mode=browse&sel=10008627" target="_blank">Csámpai Antal ✉ (<span class="authorship-author-name">Csámpai Antal</span> <span class="authorAux-mtmt"> Szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Eötvös Loránd Tudományegyetem">ELTE</span>/<span title="Természettudományi Kar">TTK</span>/<span title="Kémiai Intézet">KI</span>/Szerves Kémiai Tanszék</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;33154738" target="_blank">Synthesis and SAR Analysis of Novel 4-Hydroxytamoxifen Analogues Based on Their Cytotoxic Activity and Electron-Donor Character</a></div> <div> <span class="journal-title">MOLECULES</span> <span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a>)</span>: <span class="journal-volume">27</span> <span class="journal-issue">19</span> <span class="page"> Paper 6758. 24 p. </span> <span class="year">(2022)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.3390/molecules27196758" target="_blank" href="https://doi.org/10.3390/molecules27196758"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000866916400001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000866916400001"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85139847578" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85139847578"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="36235291" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=36235291&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="https://www.mdpi.com/1420-3049/27/19/6758" target="_blank" href="https://www.mdpi.com/1420-3049/27/19/6758"> Egyéb URL </a> </span> </span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 2</span> | Független: 2 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | WoS/Scopus jelölt: 2 | DOI jelölt: 2 </div> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;33154738&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 5 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 33154738</span> | <span class="status-data status-VALIDATED"> Egyeztetett </span> Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">kézi felvitel</span> </div> <div class="lastModified">Utolsó módosítás: 2024.02.09. 20:16 Jernei-Duró Cintia (Szerves kémia) </div> </div></div>