Synthesis of nitrogen-containing derivatives of 17(20)-pregnenoic, 17β-hydroxypregnanoic, and 17α-hydroxypregnanoic acids as new potential antiandrogens
- Authors: Zolottsev V.A.1, Kostin V.A.1, Novikov R.A.2, Tkachev Y.V.2, Zavialova M.G.1, Taratynova M.O.1, Latysheva A.S.1, Zazulina O.V.1, Timofeev V.P.2, Misharin A.Y.1
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Affiliations:
- V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
- V. A. Engelhardt Institute of Molecular Biology of Russian Academy of Sciences
- Issue: Vol 67, No 4 (2018)
- Pages: 667-681
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/242431
- DOI: https://doi.org/10.1007/s11172-018-2121-8
- ID: 242431
Cite item
Abstract
A general scheme for the synthesis of oxazoline and benzoxazole derivatives of [17(20)E]-21-norpregnene differing in the structure of the steroid moiety as well as amides of 17β-hydroxy-3-oxopregn-4-en-21-oic and 17α-hydroxy-3-oxopregn-4-en-21-oic acids was developed. The scheme involved synthesis of the steroid building blocks (appropriately protected derivatives of pregn-17(20)-en-21-oic, 17β-hydroxypregnan-21-oic, and 17α-hydroxypregnan-21-oic acids) and subsequent transformation of these building blocks into the target compounds. Following the developed scheme, synthesis of new nitrogen-containing steroid derivatives exhibiting antiandrogenic activity was enabled.
About the authors
V. A. Zolottsev
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Author for correspondence.
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
V. A. Kostin
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
R. A. Novikov
V. A. Engelhardt Institute of Molecular Biology of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 32 ul. Vavilova, Moscow, Russian Federation, 119991
Ya. V. Tkachev
V. A. Engelhardt Institute of Molecular Biology of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 32 ul. Vavilova, Moscow, Russian Federation, 119991
M. G. Zavialova
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
M. O. Taratynova
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
A. S. Latysheva
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
O. V. Zazulina
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121
V. P. Timofeev
V. A. Engelhardt Institute of Molecular Biology of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 32 ul. Vavilova, Moscow, Russian Federation, 119991
A. Yu. Misharin
V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences
Email: vazolottsev@mail.ru
Russian Federation, 10, Build. 8 ul. Pogodinskaya, Moscow, Russian Federation, 119121