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

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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.

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Authors and Affiliations

  1. V. N. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Sciences, 10, Build. 8 ul. Pogodinskaya, 119121, Moscow, Russian Federation, Russia

    V. A. Zolottsev, V. A. Kostin, M. G. Zavialova, M. O. Taratynova, A. S. Latysheva, O. V. Zazulina & A. Yu. Misharin

  2. V. A. Engelhardt Institute of Molecular Biology of Russian Academy of Sciences, 32 ul. Vavilova, 119991, Moscow, Russian Federation, Russia

    R. A. Novikov, Ya. V. Tkachev & V. P. Timofeev

Authors
  1. V. A. Zolottsev
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  2. V. A. Kostin
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  3. R. A. Novikov
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  4. Ya. V. Tkachev
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  5. M. G. Zavialova
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  6. M. O. Taratynova
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  7. A. S. Latysheva
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  8. O. V. Zazulina
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  9. V. P. Timofeev
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  10. A. Yu. Misharin
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Corresponding author

Correspondence to V. A. Zolottsev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0667–0681, April, 2018.

Based on the materials of the III Interdisciplinary Symposium on Medicinal, Organic, Biological Chemistry and Pharmaceuticals (MOBI-ChemPharma-2017; May 28–31, 2017; Sevastopol, Russia).

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Zolottsev, V.A., Kostin, V.A., Novikov, R.A. et al. Synthesis of nitrogen-containing derivatives of 17(20)-pregnenoic, 17β-hydroxypregnanoic, and 17α-hydroxypregnanoic acids as new potential antiandrogens. Russ Chem Bull 67, 667–681 (2018). https://doi.org/10.1007/s11172-018-2121-8

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  • DOI: https://doi.org/10.1007/s11172-018-2121-8

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