@article{MTMT:2939481, title = {Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides on d-secoestrone scaffolds}, url = {https://m2.mtmt.hu/api/publication/2939481}, author = {Szabó, Johanna and Bacsa, Ildikó and Wölfling, János and Schneider, Gyula and Zupkó, István and Varga, Mónika and Herman, Bianka Edina and Kalmár, László and Szécsi, Mihály and Mernyák, Erzsébet}, doi = {10.3109/14756366.2015.1050008}, journal-iso = {J ENZYM INHIB MED CH}, journal = {JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY}, volume = {31}, unique-id = {2939481}, issn = {1475-6366}, year = {2016}, eissn = {1475-6374}, pages = {574-579}, orcid-numbers = {Bacsa, Ildikó/0000-0001-8277-631X; Wölfling, János/0000-0002-3037-309X; Zupkó, István/0000-0003-3243-5300; Szécsi, Mihály/0000-0002-4272-1362; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:2994658, title = {Synthesis of A-ring halogenated 13alpha-estrone derivatives as potential 17beta-HSD1 inhibitors}, url = {https://m2.mtmt.hu/api/publication/2994658}, author = {Bacsa, Ildikó and Jójárt, Rebeka and Schneider, Gyula and Wölfling, János and Maróti, Péter and Herman, Bianka Edina and Szécsi, Mihály and Mernyák, Erzsébet}, doi = {10.1016/j.steroids.2015.10.008}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {104}, unique-id = {2994658}, issn = {0039-128X}, abstract = {13alpha-Estrone and its 3-methyl or benzyl ether were halogenated in ring A with N-bromo- or N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin as electrophile triggers. The chemo- and regioselectivities of the reactions depended greatly on the nature of the substituent on C-3. Bromination of the ethers led to 2- and 4-regioisomers. Bis-halogenation occurred only in the case of the phenolic derivative. Iodination and bromination resulted in similar products, except that the 3-benzyl ether could not be iodinated under the applied conditions. The potential inhibitory action of the new halogenated 13alpha-estrones on human 17beta-hydroxysteroid dehydrogenase 1 activity was investigated via in vitro radiosubstrate incubation. Some compounds proved to be effective inhibitors, with IC50 values in the submicromolar range.}, year = {2015}, eissn = {1878-5867}, pages = {230-236}, orcid-numbers = {Bacsa, Ildikó/0000-0001-8277-631X; Wölfling, János/0000-0002-3037-309X; Szécsi, Mihály/0000-0002-4272-1362; Mernyák, Erzsébet/0000-0003-4494-1817} } @article{MTMT:2602154, title = {Syntheses and Antiproliferative Effects of D-homo- and D-secoestrones}, url = {https://m2.mtmt.hu/api/publication/2602154}, author = {Mernyák, Erzsébet and Szabó, Johanna and Bacsa, Ildikó and Huber, Judit and Schneider, Gyula and Minorics, Renáta and Bózsity-Faragó, Noémi and Zupkó, István and Varga, Mónika and Bikádi, Zsolt and Hazai, Eszter and Wölfling, János}, doi = {10.1016/j.steroids.2014.05.015}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {87}, unique-id = {2602154}, issn = {0039-128X}, abstract = {Abstract Substituted and/or heterocyclic D-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-D-secoaldehyde, -D-secoalcohol or -D-secocarboxylic acid of estrone 3-benzyl ether. The D-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new D-homo- and D-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. D-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two D-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.}, keywords = {HomoestroneSecoestroneAntiproliferative effectMTT assayTubulin polymerization}, year = {2014}, eissn = {1878-5867}, pages = {128-136}, orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817; Bacsa, Ildikó/0000-0001-8277-631X; Minorics, Renáta/0000-0001-9685-813X; Zupkó, István/0000-0003-3243-5300; Wölfling, János/0000-0002-3037-309X} } @article{MTMT:2720405, title = {Synthesis and in vitro antiproliferative evaluation of D-secooxime derivatives of 13β- and 13α-estrone}, url = {https://m2.mtmt.hu/api/publication/2720405}, author = {Mernyák, Erzsébet and Fiser, Gabriella and Szabó, Johanna and Bodnár, Brigitta and Schneider, Gyula and Kovács, Ida Jusztina and Ocsovszki, Imre and Zupkó, István and Wölfling, János}, doi = {10.1016/j.steroids.2014.08.015}, journal-iso = {STEROIDS}, journal = {STEROIDS}, volume = {89}, unique-id = {2720405}, issn = {0039-128X}, abstract = {Abstract D-Secooximes were synthesized from the D-secoaldehydes in the 13β- and 13α-estrone series. The oximes were modified at three sites in the molecule: the oxime function was transformed into an oxime ether, oxime ester or nitrile group, the propenyl side-chain was saturated and the 3-benzyl ether was removed in order to obtain a phenolic hydroxy function. Triazoles were formed via Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC) from 3-(prop-2-yniloxy)-D-secooximes and benzylazides. All the products were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7, A2780 and A431). Some of them exhibited activities with submicromolar IC50 values, better than that of the reference agent cisplatin. The structural modifications led to significant differences in the cytostatic properties. Flow cytometry indicated that one of the most potent agents resulted in a cell cycle blockade.}, keywords = {oxime; Antitumor activity; Secoestrone; Cell cycle blocade; 13α-estrone}, year = {2014}, eissn = {1878-5867}, pages = {47-55}, orcid-numbers = {Mernyák, Erzsébet/0000-0003-4494-1817; Ocsovszki, Imre/0000-0003-1290-996X; Zupkó, István/0000-0003-3243-5300; Wölfling, János/0000-0002-3037-309X} }