Synthesis and cytotoxicity of 17E-(2-aryl-2-oxo-1-ethylidene)-5α-androstane derivatives

被引：17

作者：

Li, Yan ^{[1
]}

Huang, Jie ^{[1
]}

Liu, Jinliang ^{[1
]}

Yan, Peiyun ^{[1
]}

Liu, Hui ^{[1
]}

Sun, Qian ^{[1
]}

Wang, Xingbin ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Peoples R China

来源：

STEROIDS | 2011年 / 76卷 / 14期

基金：

中国国家自然科学基金;

关键词：

Epiandrosterone; 17E-(2-aryl-2-oxo-1-ethylidene)-5 alpha-androstane; Meyer-Schuster rearrangement; Mercury sulfate; Anticancer activity; PROPARGYLIC ALCOHOLS; ANTICANCER AGENTS; ISOMERIZATION; STEROIDS; ELUCIDATION;

D O I：

10.1016/j.steroids.2011.10.003

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：

The efficient synthesis of some 17E-(2-aryl-2-oxo-1-ethylidene)-5 alpha-androstan-3 beta-ols was investigated. 17-Alkynyl-3,17-androstanediols were prepared through the nucleophilic addition of epiandrosterone using the corresponding 1-alkynes in the presence of a strong base n-BuLi firstly. The Meyer-Schuster rearrangement of 17-alkynyl-3,17-androstanediols was carried out efficiently catalyzed by 10% H2SO4 and HgSO4 in THF. This strategy offered a very straightforward and efficient method for access to conjugated alpha,beta-unsaturated ketone 17E,5 alpha-androstan-3 beta-ols from the 17-alkyny1-3,17-androstanediols in good overall yields, which are key intermediates for the preparation of some biologically important modified 17-side chain steroids. Evaluation of the synthesized compounds for cytotoxicity against A549, SKOV3, MKN-45 and MDA-MB-435 cell lines showed that 17E-(2-aryl-2-oxo-1-ethylidene)-5 alpha-androstanes possessing a hydroxyl groups at C-3 and fluoro-substituted group of aromatic ring in the side chain have significant inhibition activity. (C) 2011 Elsevier Inc. All rights reserved.

引用

页码：1615 / 1620

页数：6

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