New azole derivatives of [17(20)E]-21-norpregnene: Synthesis and inhibition of prostate carcinoma cell growth

Tatsiana S. Dalidovich, Alaksiej L. Hurski, Galina E. Morozevich, Alexandra S. Latysheva, Tatsiana A. Sushko, Natallia V. Strushkevich, Andrei A. Gilep, Alexander Y. Misharin, Vladimir N. Zhabinskii, Vladimir A. Khripach

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A number of isoxazole, 1,2,3-triazole, tetrazole, and 1,2,4-oxadiazole derivatives of [17(20)E]-21-norpregnene comprising 3β-hydroxy-5-ene and 3-oxo-4-ene fragments were prepared. Among the key steps for the synthesis of isoxazoles, 1,2,3-triazoles, and tetrazoles were (i)1,3-dipolar cycloaddition of nitrile oxides or azides to acetylenes or nitriles and ii)dehydration of 17β-hydroxy-17α-methylene-azoles to [17(20)E]-21-norpregnene derivatives. 1,2,4-Oxadiazoles were prepared through the formation of acetimidamides. Potency of the synthesized compounds to inhibit CYP17A1 and to suppress growth of prostate carcinoma cells was investigated. Among the new azole derivatives, four compounds were found possessing high anti-proliferative activity.

Original languageEnglish
Pages (from-to)10-18
Number of pages9
JournalSteroids
Volume147
DOIs
Publication statusPublished - Jul 2019
Externally publishedYes

Keywords

  • Azoles
  • CYP17A1 inhibitors
  • LNCaP prostate carcinoma cells
  • PC-3 prostate carcinoma cells
  • [17(20)E]-21-Norpregnenes

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