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<p>Possible metabolites of progestin 16α, 17α-cyclohexaprogesterone <b>1</b>, namely, 3α-hydroxy-, 3β-hydroxy-16α, 17α-cyclohexapregn-4-en-20-one, and 3α-hydroxy-16α, 17α-cyclohexa-5α-pregnan-20-one, were synthesized by reduction of the 3-keto group and subsequent Mitsunobu type inversion of configuration of the obtained alcohols. Study of the antiproliferative activity of the synthesized compounds and progestin <b>1</b> against MCF-7 and T47D cells in hormone-dependent breast cancer showed that the obtained steroids with a double bond in ring A retain the antiproliferative activity of progestin <b>1</b> with an IC<sub>50</sub> of 22–34 µmol L<sup>−1</sup>, while the 5α-reduced analogs are practically inactive at doses up to 50 µmol L<sup>−1</sup>.</p>

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Synthesis of possible metabolites of 16α, 17α-cyclohexaprogesterone and evaluation of their antiproliferative activity in hormone-dependent breast cancer cell lines

  • 期刊论文

  • 发表日期：

    2025年8月1日

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  • M. O. Tserfas,
  • F. B. Bogdanov,
  • A. L. Mikhaylova,
  • Yu. V. Kuznetsov,
  • I. V. Zavarzin,
  • A. M. Scherbakov,
  • I. S. Levina

摘要

Possible metabolites of progestin 16α, 17α-cyclohexaprogesterone 1, namely, 3α-hydroxy-, 3β-hydroxy-16α, 17α-cyclohexapregn-4-en-20-one, and 3α-hydroxy-16α, 17α-cyclohexa-5α-pregnan-20-one, were synthesized by reduction of the 3-keto group and subsequent Mitsunobu type inversion of configuration of the obtained alcohols. Study of the antiproliferative activity of the synthesized compounds and progestin 1 against MCF-7 and T47D cells in hormone-dependent breast cancer showed that the obtained steroids with a double bond in ring A retain the antiproliferative activity of progestin 1 with an IC50 of 22–34 µmol L−1, while the 5α-reduced analogs are practically inactive at doses up to 50 µmol L−1.