Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-one analogues

被引：9
作者：
Wang, Cunde [1 ]
Liu, Lanhai [1 ]
Xu, Hangxian [1 ]
Zhang, Zonglei [1 ]
Wang, Xingbin [1 ]
Liu, Hui [1 ]
机构：
[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
来源：
STEROIDS | 2011年 / 76卷 / 05期
关键词：
Cyclo-18,21-dinorcholenones; Iodine; Palladium(0) catalyst; Cuprous iodide; Sonogashira reaction; ARYL IODIDES; ALKYNES; DERIVATIVES; STEROIDS;
D O I：
10.1016/j.steroids.2011.01.005
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 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-ones was investigated. 22-Iodocyclo-18,21-dinorcholenones were prepared from cyclo-18,21-dinorcholenones using I(2)/DMAP/pyridine system firstly. The cross coupling reaction of 22-iodocyclo-18,21-dinorcholenones and 1-alkynes was carried out efficiently catalyzed by tetrakis(triphenylphosphine) palladium/cuprous iodide in the presence of base diisopropylethylamine. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cyclo-18,21-dinorcholenones from the cyclo-18,21-dinorcholenones and 1-alkynes in excellent overall yields. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa, MKN-28 and MCF-7 cell lines showed that the 22-alkynylcyclodinorchoenones possessing hydroxylethyl and hyclroxylmethyl mono-substituted side chain at the end of alkynyl group have significantly inhibition activity. (C) 2011 Elsevier Inc. All rights reserved.
引用
收藏
页码：491 / 496
页数：6
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