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

被引：9

作者：

Dalidovich, Tatsiana S. ^{[1
]}

Hurski, Alaksiej L. ^{[1
]}

Morozevich, Galina E. ^{[2
]}

Latysheva, Alexandra S. ^{[2
]}

Sushko, Tatsiana A. ^{[1
,3
]}

Strushkevich, Natallia V. ^{[1
]}

Gilep, Andrei A. ^{[1
]}

Misharin, Alexander Y. ^{[2
]}

Zhabinskii, Vladimir N. ^{[1
]}

Khripach, Vladimir A. ^{[1
]}

机构：

[1] Natl Acad Sci Belarus, Inst Bioorgan Chem, Kuprevich Str 5-2, Minsk 220141, BELARUS

[2] Orekhovich Inst Biomed Chem, Moscow, Russia

[3] Univ Tokyo, Sch Engn, Dept Bioengn, Tokyo, Japan

来源：

STEROIDS | 2019年 / 147卷

关键词：

Azoles; 17(20)E]-21-Norpregnenes; CYP17A1; inhibitors; LNCaP prostate carcinoma cells; PC-3 prostate carcinoma cells; 17-ALPHA-HYDROXYLASE-C-17; C-20-LYASE P450(17-ALPHA); OXAZOLINYL DERIVATIVES; ANDROSTANE DERIVATIVES; STEROIDAL INHIBITORS; ANDROGEN RECEPTOR; POTENTIAL AGENTS; CYP17A1; CANCER; ABIRATERONE; 1,2,3-TRIAZOLES;

D O I：

10.1016/j.steroids.2018.08.004

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A number of isoxazole, 1,2,3-triazole, tetrazole, and 1,2,4-oxadiazole derivatives of [17(20)E]-21-norpregnene comprising 3 beta-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 beta-hydroxy-17a-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.

引用

页码：10 / 18

页数：9

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