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Russian Chemical Bulletin

, Volume 54, Issue 11, pp 2664–2670 | Cite as

Synthesis of 19-substituted steroids of the 16α,17α-cyclohexanopregnane series and study of their interactions with rat uterine cytosol and blood serum proteins

  • I. S. Levina
  • L. E. Kulikova
  • A. V. Kamernitsky
  • E. V. Pokrovskaya
  • A. N. Smirnov
Article

Abstract

New 16α,17α-cyclohexanopregnanes (pregna-D′6-pentaranes) containing alkyl or heteroatomic substituents in position 19, namely, 19-methylidene-, 19-methyl-, 19-methoxyimino-, and 19-(3-methoxycarbonylpropoxyimino)-16α,17α-cyclohexanopregn-4-ene-3,20-diones were synthesized, and their interactions with the progesterone receptor and pentarane-binding proteins of rat uterus cytosol and rat blood serum was studied. The same substituent in position 19 of the steroid molecule can affect in opposite direction its affinity to these proteins. These results suggest differences in the structures of the ligand-binding pockets of the three proteins in the region surrounding the C(10) atom of the steroid nucleus.

Key words

Wittig reaction pentaranes progesterone binding receptor 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • I. S. Levina
    • 1
  • L. E. Kulikova
    • 1
  • A. V. Kamernitsky
    • 1
  • E. V. Pokrovskaya
    • 2
  • A. N. Smirnov
    • 2
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Department of BiologyM. V. Lomonosov Moscow State UniversityMoscowRussian Federation

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