Synthesis of Novel Anion Recognition Molecules as Quinazoline Precursors

https://m2.mtmt.hu/ hun 2026-09-23 10:26 JournalArticle 36490998 VALIDATED true 0 false 2026-07-22T07:11:21.602+0000 2026-04-27T13:57:51.048+0000 2025-12-13T10:03:16.912+0000 true 10015206 Áncsán Gizella /api/admin/10015206 Admin Áncsán Gizella (SE admin) true 10015206 2026-04-27T13:57:51.334+0000 2026-04-27T13:57:51.334+0000 2026-01-12T09:15:30.820+0000 true 10062250 Molnár-Taga Márta /api/admin/10062250 Admin Molnár-Taga Márta (SE 4-es admin) true 10062250 Admin 10065569 /api/admin/10065569 Pécsi Éva (MTMT Közp 2,3, admin) Pécsi Éva true true 2026-04-14T13:01:34.757+0000 true false true 24 24 /api/publicationtype/24 PublicationType Folyóiratcikk 1 true 24 JournalArticle true 10000059 Article true 24 24 /api/publicationtype/24 PublicationType Folyóiratcikk 1 true 24 JournalArticle /api/subtype/10000059 Szakcikk SubType Szakcikk (Folyóiratcikk) 101 true 10000059 true 1 /api/category/1 Category Tudományos true 1 Krajsovszky, Gábor Synthesis of Novel Anion Recognition Molecules as Quinazoline Precursors true true /api/journal/10003252 REVIEWED INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 1661-6596 1422-0067 true false 10003252 false 10003252 true 1661-6596 1422-0067 Journal FOREIGN 26 24 11975 11975 11 2025 Thiourea and structurally related urea derivatives are widely recognised for their ability to transport anions through hydrogen bonding interactions. The strength of these interactions correlates with the electronegativity of the ligand and the acidity of the NH hydrogens involved. Thiourea, being more acidic than urea, exhibits partial deprotonation in the presence of certain anions such as organic carboxylates, fluoride, and bromide, while remaining resistant to deprotonation by chloride. This behaviour suggests a degree of selectivity toward chloride ions. Additionally, while carbamide-containing molecules tend to aggregate—potentially reducing their ion-binding efficiency—thiourea derivatives show reduced aggregation, preserving their binding capabilities. In this study, we report the synthesis and characterisation of 21 novel thiourea derivatives obtained by reacting 2-aminobenzoylamino acid esters with various substituted phenyl isothiocyanates. Seven similar thiourea-containing molecules were made as a comparison—without the amino acids—by reacting aniline with the different phenyl isothiocyanates. The reaction kinetics were found to be influenced primarily by the electronic nature of the substituents on the phenyl ring. Electron-withdrawing groups (EWGs), such as para-nitro, 3,5-bis(trifluoromethyl), and fluorine, accelerated the reaction, while electron-donating groups (EDGs), such as para-methoxy, slowed it down. Interestingly, the nature of the amino acid precursors had no significant impact on reaction time; however, reactions with aniline proceeded the fastest. Solvent choice also played a role: reactions in N,N-dimethylformamide (DMF) proceeded faster than in acetone, although with reduced yields. Consequently, reaction conditions were optimised to balance time efficiency and product yield. To evaluate the chloride ion-binding properties of the synthesised compounds, 1H NMR titration experiments were conducted in deuterated dimethyl sulfoxide (DMSO-d6). The association constants (Ka) derived from these studies revealed a clear correlation with the electronic nature of the substituents. Compounds bearing EWGs exhibited enhanced chloride binding, while those with EDGs showed diminished binding affinity. Surprisingly, the presence of amino acid moieties led to a decrease in Ka values, despite the electron-withdrawing nature of the amide groups. This suggests that steric or conformational factors may play a role in modulating binding strength. Overall, the synthesised thiourea derivatives demonstrate mild, reversible chloride ion-binding behaviour, making them promising candidates for further development as selective anion receptors. The insights gained from this study contribute to a deeper understanding of structure–activity relationships in anion-binding systems and may inform the design of future supramolecular architectures with tailored ion recognition properties. Funding 2061390 /api/funding/2061390 OTKA(ANN 139484) false true Funding 2061391 /api/funding/2061391 (TKP2021-EGA-31) false true Funding 2061392 /api/funding/2061392 Nemzeti Gyógyszerkutatási és Fejlesztési Laboratórium (PharmaLab)(RRF-2.3.1-21-2022-00015) Támogató: NKFIH false true true true 2025 true true true false true false GOLD 2026-07-22 true https://repo.lib.semmelweis.hu/handle/123456789/10449 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 D1 false 10022276 false false false 2026-01-06T10:49:45.372+0000 Gyógyszerészi Kémiai Intézet (SE / GYTK); Szerkezetkutató Központ (HRN TTK); Szerves Vegytani Intézet (SE / GYTK) 7 33 3 8 0 true 10065569 Language 10002 /api/language/10002 Angol Angol English true 2 true PersonAuthorship 128876574 /api/authorship/128876574 Krajsovszky, Gábor [Krajsovszky, Gábor (Szerves-és gyógys...), szerző] Szerves Vegytani Intézet (SE / GYTK) 1 0.125 true false false Author 10022276 /api/author/10022276 Krajsovszky Gábor (Szerves-és gyógyszerkémia) Krajsovszky Gábor DUPLUM true 10022276 true Krajsovszky Gábor true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876575 /api/authorship/128876575 Piros, László* [Piros, László (szerves kémia), szerző] Szerves Vegytani Intézet (SE / GYTK) 2 0.125 true false false Author 10094645 /api/author/10094645 Piros László (szerves kémia) Piros László true true Piros László true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876576 /api/authorship/128876576 Bogdán, Dóra [Bogdán, Dóra (Szerves kémia, gy...), szerző] Szerves Vegytani Intézet (SE / GYTK) 3 0.125 false false false Author 10049468 /api/author/10049468 Bogdán Dóra (Szerves kémia, gyógyszerkémia) Bogdán Dóra true 10049468 true Bogdán Dóra true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876577 /api/authorship/128876577 Kalydi, Eszter [Kalydi, Eszter (NMR spektroszkópia), szerző] Szerves Vegytani Intézet (SE / GYTK) 4 0.125 false false false Author 10070197 /api/author/10070197 Kalydi Eszter (NMR spektroszkópia) Kalydi Eszter true true Kalydi Eszter true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876578 /api/authorship/128876578 Gáti, Tamás 5 0.125 false false false Gáti Tamás true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876579 /api/authorship/128876579 Szabó, Pál [Szabó, Pál Tamás (Tömegspektrometria), szerző] Szerkezetkutató Központ (HRN TTK) 6 0.125 false false false Author 10014589 /api/author/10014589 Szabó Pál Tamás (Tömegspektrometria) Szabó Pál Tamás true 10014589 true Szabó Pál true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876580 /api/authorship/128876580 Horváth, Péter [Horváth, Péter (cirkuláris dikroi...), szerző] Gyógyszerészi Kémiai Intézet (SE / GYTK) 7 0.125 false false false Author 10020177 /api/author/10020177 Horváth Péter (cirkuláris dikroizmus, HPLC) Horváth Péter true 10020177 true Horváth Péter true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PersonAuthorship 128876581 /api/authorship/128876581 Mándity, István M. ✉ [Mándity, István (Gyógyszerkémia, g...), szerző] Szerves Vegytani Intézet (SE / GYTK) 8 0.125 false true true Author 10022837 /api/author/10022837 Mándity István (Gyógyszerkémia, gyógyszerkutatás) Mándity István true 10022837 true Mándity István M. true false false AuthorshipType 1 /api/authorshiptype/1 Szerző 0 true 0 true false true PublicationIdentifier 30320363 /api/publicationidentifier/30320363 DOI: 10.3390/ijms262411975 PlainSource 6 /api/publicationsource/6 DOI PublicationSourceType 10001 /api/publicationsourcetype/10001 DOI true true true DOI DOI https://doi.org/@@@ true true 6 true IDENTICAL 10.3390/ijms262411975 https://doi.org/10.3390/ijms262411975 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(2025) INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 1661-6596 1422-0067 26 24<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="10022276"><a href="/gui2/?type=authors&mode=browse&sel=10022276" target="_blank">Krajsovszky Gábor (<span class="authorship-author-name">Krajsovszky Gábor</span> <span class="authorAux-mtmt"> Szerves-és gyógyszerkémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Szerves Vegytani Intézet</span> ;    <span class="author-name" mtid="10094645"><a href="/gui2/?type=authors&mode=browse&sel=10094645" target="_blank">Piros László<sup>*</sup> (<span class="authorship-author-name">Piros László</span> <span class="authorAux-mtmt"> szerves kémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Szerves Vegytani Intézet</span> ;    <span class="author-name" mtid="10049468"><a href="/gui2/?type=authors&mode=browse&sel=10049468" target="_blank">Bogdán Dóra (<span class="authorship-author-name">Bogdán Dóra</span> <span class="authorAux-mtmt"> Szerves kémia, gyógyszerkémia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Szerves Vegytani Intézet</span> ;    <span class="author-name" mtid="10070197"><a href="/gui2/?type=authors&mode=browse&sel=10070197" target="_blank">Kalydi Eszter (<span class="authorship-author-name">Kalydi Eszter</span> <span class="authorAux-mtmt"> NMR spektroszkópia</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Szerves Vegytani Intézet</span> ;    <span class="author-name" >Gáti Tamás </span> ;    <span class="author-name" mtid="10014589"><a href="/gui2/?type=authors&mode=browse&sel=10014589" target="_blank">Szabó Pál (<span class="authorship-author-name">Szabó Pál Tamás</span> <span class="authorAux-mtmt"> Tömegspektrometria</span>) </a> </span> <span class="author-affil"><span title="HUN-REN Természettudományi Kutatóközpont">HRN TTK</span>/Szerkezetkutató Központ</span> ;    <span class="author-name" mtid="10020177"><a href="/gui2/?type=authors&mode=browse&sel=10020177" target="_blank">Horváth Péter (<span class="authorship-author-name">Horváth Péter</span> <span class="authorAux-mtmt"> cirkuláris dikroizmus, HPLC</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerészi Kémiai Intézet</span> ;    <span class="author-name" mtid="10022837"><a href="/gui2/?type=authors&mode=browse&sel=10022837" target="_blank">Mándity István M. ✉ (<span class="authorship-author-name">Mándity István</span> <span class="authorAux-mtmt"> Gyógyszerkémia, gyógyszerkutatás</span>) </a> </span> <span class="author-affil"><span title="Semmelweis Egyetem">SE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Szerves Vegytani Intézet</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse&params=publication;36490998" target="_blank">Synthesis of Novel Anion Recognition Molecules as Quinazoline Precursors</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">26</span> <span class="journal-issue">24</span> <span class="page"> Paper 11975. 11 p. </span> <span class="year">(2025)</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_none" title="none"> <a style="color:blue" title="10.3390/ijms262411975" target="_blank" href="https://doi.org/10.3390/ijms262411975"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="001646800400001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/001646800400001"> WoS </a> </span> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:black" title="10449" target="_blank" href="https://repo.lib.semmelweis.hu/handle/123456789/10449"> SE Repozitórium </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="105025779013" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-105025779013"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="41465402" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=41465402&dopt=Abstract"> PubMed </a> </span> </span> <OnlyViewableByAuthor><div class="ratings"> <div class="journal-subject">Folyóirat szakterülete: Scopus - Inorganic Chemistry   SJR indikátor: D1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Organic Chemistry   SJR indikátor: D1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Spectroscopy   SJR indikátor: D1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Catalysis   SJR indikátor: Q1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Computer Science Applications   SJR indikátor: Q1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Medicine (miscellaneous)   SJR indikátor: Q1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Physical and Theoretical Chemistry   SJR indikátor: Q1</div> <div class="journal-subject">Folyóirat szakterülete: Scopus - Molecular Biology   SJR indikátor: Q2</div> </div></OnlyViewableByAuthor> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;36490998&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 1 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 36490998</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">WoS-XML</span> </div> <div class="funder"> OTKA(ANN 139484), (TKP2021-EGA-31), Nemzeti Gyógyszerkutatási és Fejlesztési Laboratórium (PharmaLab)(RRF-2.3.1-21-2022-00015) Támogató: NKFIH </div> <div class="lastModified">Utolsó módosítás: 2026.04.27. 15:57 Balázs András (MTMT Központ, admin) </div> <div class="lockedBy">Központi kezelésű 2026.04.14. 15:01 Pécsi Éva (MTMT Közp 2,3, admin) </div> </div></div>