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Russian Chemical Bulletin

, Volume 67, Issue 4, pp 667–681 | Cite as

Synthesis of nitrogen-containing derivatives of 17(20)-pregnenoic, 17β-hydroxypregnanoic, and 17α-hydroxypregnanoic acids as new potential antiandrogens

  • V. A. Zolottsev
  • V. A. Kostin
  • R. A. Novikov
  • Ya. V. Tkachev
  • M. G. Zavialova
  • M. O. Taratynova
  • A. S. Latysheva
  • O. V. Zazulina
  • V. P. Timofeev
  • A. Yu. Misharin
Full Article
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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.

Key words

steroids synthesis antiandrogens CYP17A1 inhibitors 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. A. Zolottsev
    • 1
  • V. A. Kostin
    • 1
  • R. A. Novikov
    • 2
  • Ya. V. Tkachev
    • 2
  • M. G. Zavialova
    • 1
  • M. O. Taratynova
    • 1
  • A. S. Latysheva
    • 1
  • O. V. Zazulina
    • 1
  • V. P. Timofeev
    • 2
  • A. Yu. Misharin
    • 1
  1. 1.V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of SciencesMoscow, Russian FederationRussia
  2. 2.V. A. Engelhardt Institute of Molecular Biology of Russian Academy of SciencesMoscow, Russian FederationRussia

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