TY - JOUR AU - Szabó, Johanna AU - Bacsa, Ildikó AU - Wölfling, János AU - Schneider, Gyula AU - Zupkó, István AU - Varga, Mónika AU - Herman, Bianka Edina AU - Kalmár, László AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides on d-secoestrone scaffolds JF - JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY J2 - J ENZYM INHIB MED CH VL - 31 PY - 2016 IS - 4 SP - 574 EP - 579 PG - 6 SN - 1475-6366 DO - 10.3109/14756366.2015.1050008 UR - https://m2.mtmt.hu/api/publication/2939481 ID - 2939481 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary Cereal Research Non-Profit Ltd., Szeged, Hungary 1st Department of Medicine, University of Szeged, Szeged, Hungary Department of Obstetrics and Gynecology, University of Szeged, Szeged, Hungary Cited By :14 Export Date: 23 February 2021 CODEN: JEIMA Correspondence Address: Mernyák, E.; Department of Organic Chemistry, Dóm tér 8, Hungary; email: bobe@chem.u-szeged.hu Chemicals/CAS: amide, 17655-31-1; cisplatin, 15663-27-1, 26035-31-4, 96081-74-2; estradiol 17beta dehydrogenase, 9028-61-9; estrone, 53-16-7; Antineoplastic Agents; Benzyl Compounds; D-secoestrone; Enzyme Inhibitors; Estradiol Dehydrogenases; Estrone; HSD17B1 protein, human; N-((1-benzyl-1,2,3-triazol-4-yl)methyl)carboxamide; Triazoles LA - English DB - MTMT ER - TY - JOUR AU - Bacsa, Ildikó AU - Jójárt, Rebeka AU - Schneider, Gyula AU - Wölfling, János AU - Maróti, Péter AU - Herman, Bianka Edina AU - Szécsi, Mihály AU - Mernyák, Erzsébet TI - Synthesis of A-ring halogenated 13alpha-estrone derivatives as potential 17beta-HSD1 inhibitors JF - STEROIDS J2 - STEROIDS VL - 104 PY - 2015 SP - 230 EP - 236 PG - 7 SN - 0039-128X DO - 10.1016/j.steroids.2015.10.008 UR - https://m2.mtmt.hu/api/publication/2994658 ID - 2994658 N1 - Department of Organic Chemistry, University of Szeged, Dóm tér 8., Szeged, H-6720, Hungary 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Cited By :9 Export Date: 30 August 2019 CODEN: STEDA Correspondence Address: Szécsi, M.; 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, Hungary; email: szecsi.mihaly@med.u-szeged.hu Chemicals/CAS: testosterone 17beta dehydrogenase, 9028-62-0; estradiol 17beta dehydrogenase, 9028-61-9; estrone, 53-16-7; Enzyme Inhibitors; Estradiol Dehydrogenases; Estrone; HSD17B1 protein, human Funding details: Országos Tudományos Kutatási Alapprogramok, OTKA, K113150 Funding Agency and Grant Number: Hungarian Scientific Research FundOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA K113150]; Richter Gedeon Plc. Funding text: The authors are grateful for financial support from the Hungarian Scientific Research Fund (OTKA K113150) and Richter Gedeon Plc. Department of Organic Chemistry, University of Szeged, Dóm tér 8., Szeged, H-6720, Hungary 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, Szeged, H-6720, Hungary Cited By :10 Export Date: 10 January 2021 CODEN: STEDA Correspondence Address: Szécsi, M.; 1st Department of Medicine, University of Szeged, Korányi fasor 8-10, Hungary; email: szecsi.mihaly@med.u-szeged.hu Chemicals/CAS: testosterone 17beta dehydrogenase, 9028-62-0; estradiol 17beta dehydrogenase, 9028-61-9; estrone, 53-16-7; Enzyme Inhibitors; Estradiol Dehydrogenases; Estrone; HSD17B1 protein, human Funding details: Országos Tudományos Kutatási Alapprogramok, OTKA, K113150 AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Mernyák, Erzsébet AU - Szabó, Johanna AU - Bacsa, Ildikó AU - Huber, Judit AU - Schneider, Gyula AU - Minorics, Renáta AU - Bózsity-Faragó, Noémi AU - Zupkó, István AU - Varga, Mónika AU - Bikádi, Zsolt AU - Hazai, Eszter AU - Wölfling, János TI - Syntheses and Antiproliferative Effects of D-homo- and D-secoestrones JF - STEROIDS J2 - STEROIDS VL - 87 PY - 2014 SP - 128 EP - 136 PG - 9 SN - 0039-128X DO - 10.1016/j.steroids.2014.05.015 UR - https://m2.mtmt.hu/api/publication/2602154 ID - 2602154 AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Mernyák, Erzsébet AU - Fiser, Gabriella AU - Szabó, Johanna AU - Bodnár, Brigitta AU - Schneider, Gyula AU - Kovács, Ida Jusztina AU - Ocsovszki, Imre AU - Zupkó, István AU - Wölfling, János TI - Synthesis and in vitro antiproliferative evaluation of D-secooxime derivatives of 13β- and 13α-estrone JF - STEROIDS J2 - STEROIDS VL - 89 PY - 2014 SP - 47 EP - 55 PG - 9 SN - 0039-128X DO - 10.1016/j.steroids.2014.08.015 UR - https://m2.mtmt.hu/api/publication/2720405 ID - 2720405 N1 - CAplus AN 2014:1453570; MEDLINE PMID: 25150017 (Journal; Article; Research Support, Non-U.S. Gov't); Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Department of Biochemistry, University of Szeged, Dóm tér 9, Szeged, H-6720, Hungary Cited By :14 Export Date: 31 May 2021 CODEN: STEDA Correspondence Address: Mernyák, E.; Department of Organic Chemistry, University of Szeged, Dóm tér 8, Hungary AB - 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. LA - English DB - MTMT ER -