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

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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.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. S. Levina, L. E. Kulikova & I. V. Zavarzin

  2. N. I. Pirogov Russian National Research Medical University, 1 ul. Ostrovityanova, 117997, Moscow, Russian Federation

    A. V. Semeikin

Authors
  1. I. S. Levina
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  2. L. E. Kulikova
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  3. A. V. Semeikin
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  4. I. V. Zavarzin
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Corresponding author

Correspondence to I. S. Levina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2108–2111, November, 2018.

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Levina, I.S., Kulikova, L.E., Semeikin, A.V. et al. Synthesis of 4-hetero-16α,17α-cyclohexanopregnanes and evaluation of their cytotoxicity against the HeLa cell line. Russ Chem Bull 67, 2108–2111 (2018). https://doi.org/10.1007/s11172-018-2336-8

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  • DOI: https://doi.org/10.1007/s11172-018-2336-8

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