Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

Scholarly Works

• Quindt, M. I.; Gola, G. F.; Ramirez, J. A.; Bonesi, S. M. Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives. The Journal of organic chemistry 2023, 88, 13796–13812. doi:10.1021/acs.joc.3c01446
• Quindt, M. I.; Protti, S.; Merli, D.; Bonesi, S. M. Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300084
• Zottel, A.; Jójárt, R.; Ágoston, H.; Hafner, E.; Lipušček, N.; Mernyák, E.; Rižner, T. L. Cytotoxic effect of 13α-estrane derivatives on breast, endometrial and ovarian cancer cell lines. The Journal of steroid biochemistry and molecular biology 2023, 232, 106350. doi:10.1016/j.jsbmb.2023.106350
• Adriano, N.; Ahearn, C.; Black, C.; Cracchiolo, M.; Ghere, D.; Nuñez, A.; Olivan, L.; Patel, R.; Saner, S.; Smith, K. R.; Watkins, B.; Hare, P. M. Solvent- and Wavelength-Dependent Photolysis of Estrone. Photochemistry and photobiology 2021, 98, 783–797. doi:10.1111/php.13542
• Jójárt, R.; Laczkó-Rigó, R.; Klement, M.; Kőhl, G.; Kecskeméti, G.; Özvegy-Laczka, C.; Mernyák, E. Design, synthesis and biological evaluation of novel estrone phosphonates as high affinity organic anion-transporting polypeptide 2B1 (OATP2B1) inhibitors. Bioorganic chemistry 2021, 112, 104914. doi:10.1016/j.bioorg.2021.104914
• Traj, P.; Abdolkhaliq, A. H.; Németh, A.; Dajcs, S. T.; Tömösi, F.; Lanisnik-Rizner, T.; Zupkó, I.; Mernyák, E. Transition metal-catalysed A-ring C–H activations and C(sp2)–C(sp2) couplings in the 13α-oestrone series and in vitro evaluation of antiproliferative properties. Journal of enzyme inhibition and medicinal chemistry 2021, 36, 895–902. doi:10.1080/14756366.2021.1900165
• Mernyák, E.; Bartha, S.; Kóczán, L.; Jójárt, R.; Resch, V.; Paragi, G.; Vágvölgyi, M.; Hunyadi, A.; Bruszel, B.; Zupkó, I.; Minorics, R. Microwave-assisted Phospha-Michael addition reactions in the 13α-oestrone series and in vitro antiproliferative properties. Journal of enzyme inhibition and medicinal chemistry 2021, 36, 1931–1937. doi:10.1080/14756366.2021.1963241
• Jójárt, R.; Ali, H.; Horváth, G.; Kele, Z.; Zupkó, I.; Mernyák, E. Pd-catalyzed Suzuki-Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents. Steroids 2020, 164, 108731. doi:10.1016/j.steroids.2020.108731
• Nagymihály, Z.; Wölfling, J.; Schneider, G.; Kollár. Synthesis of 2-Methylresorcinol-Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim. ChemistrySelect 2020, 5, 6933–6938. doi:10.1002/slct.202001728
• Cheng, Y.; Yang, Y.; Wu, Y.; Wang, W.; Xiao, L.; Zhang, Y.; Tang, J.; Huang, Y.; Zhang, S.; Xiang, Q. The Curcumin Derivative, H10, Suppresses Hormone-Dependent Prostate Cancer by Inhibiting 17β-Hydroxysteroid Dehydrogenase Type 3. Frontiers in pharmacology 2020, 11, 637. doi:10.3389/fphar.2020.00637
• Laczkó-Rigó, R.; Jójárt, R.; Mernyák, E.; Bakos, É.; Tuerkova, A.; Zdrazil, B.; Özvegy-Laczka, C. Structural dissection of 13-epiestrones based on the interaction with human Organic anion-transporting polypeptide, OATP2B1. The Journal of steroid biochemistry and molecular biology 2020, 200, 105652. doi:10.1016/j.jsbmb.2020.105652
• Jójárt, R.; Pécsy, S.; Keglevich, G.; Szécsi, M.; Rigó, R.; Özvegy-Laczka, C.; Kecskeméti, G.; Mernyák, E. Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors. Beilstein journal of organic chemistry 2018, 14, 2838–2845. doi:10.3762/bjoc.14.262
• Amr, A. E.-G. E.; El-Naggar, M.; Al-Omar, M. A.; Elsayed, E. A.; Abdalla, M. M. In Vitro and In Vivo Anti-Breast Cancer Activities of Some Synthesized Pyrazolinyl-estran-17-one Candidates. Molecules (Basel, Switzerland) 2018, 23, 1572. doi:10.3390/molecules23071572
• Dewan, A.; Sarmah, M.; Thakur, A. J.; Bharali, P.; Bora, U. Greener Biogenic Approach for the Synthesis of Palladium Nanoparticles Using Papaya Peel: An Eco-Friendly Catalyst for C-C Coupling Reaction. ACS omega 2018, 3, 5327–5335. doi:10.1021/acsomega.8b00039
• Bacsa, I.; Szemerédi, D.; Wölfling, J.; Schneider, G.; Fekete, L.; Mernyák, E. The first Pd-catalyzed Buchwald-Hartwig aminations at C-2 or C-4 in the estrone series. Beilstein journal of organic chemistry 2018, 14, 998–1003. doi:10.3762/bjoc.14.85
• Bacsa, I.; Konc, C.; Orosz, A. B.; Kecskeméti, G.; Rigó, R.; Özvegy-Laczka, C.; Mernyák, E. Synthesis of Novel C-2- or C-15-Labeled BODIPY-Estrone Conjugates. Molecules (Basel, Switzerland) 2018, 23, 821. doi:10.3390/molecules23040821

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