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Russian Chemical Bulletin

, Volume 67, Issue 11, pp 2108–2111 | Cite as

Synthesis of 4-hetero-16α,17α-cyclohexanopregnanes and evaluation of their cytotoxicity against the HeLa cell line

  • I. S. LevinaEmail author
  • L. E. Kulikova
  • A. V. Semeikin
  • I. V. Zavarzin
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Abstract

The oxidation of the ring A of 16α,17α-cyclohexanoprogesterone gave 5-oxo-A-nor-3,5-secopregnan-3-oic acid. The subsequent ring A closure in the latter compound upon treatment with sodium acetate in Ac2O afforded 4-oxasteroid. The reaction with ammonium acetate in acetic acid produced 4-azasteroid. Antiproliferative activity of the resulting steroids against cervical cancer HeLa cells and the in vitro binding to the progesterone receptor were studied. The compounds cause a statistically significant decrease in viability of cervical cancer HeLa cells, having no effect on normal skin fibroblasts. The tested steroids show very low binding to the rat uterine progesterone receptor.

Key words

synthesis progestins progesterone receptor cell viability HeLa cell line 

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Copyright information

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

Authors and Affiliations

  • I. S. Levina
    • 1
    Email author
  • L. E. Kulikova
    • 1
  • A. V. Semeikin
    • 2
  • I. V. Zavarzin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.N. I. Pirogov Russian National Research Medical UniversityMoscowRussian Federation

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