Tatsiana S Dalidovich, A. Hurski, G. Morozevich
Jul 1, 2019
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Influential Citations
6
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Quality indicators
Journal
Steroids
Abstract
&NA; A number of isoxazole, 1,2,3‐triazole, tetrazole, and 1,2,4‐oxadiazole derivatives of [17(20)E]‐21‐norpregnene comprising 3&bgr;‐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 17&bgr;‐hydroxy‐17&agr;‐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. Graphical abstract Figure. No caption available.