Synthesis of (±)-2R,4R,5S-2-methoxy-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexanone and (±)-2R,4S,5R-2-methoxy-5-nitro-4-(2,3,4-trimethoxyphenyl)cyclohexanone as colchicine mimetics

被引：2

作者：

Evans, KA ^{[1
]}

Beshah, K ^{[1
]}

Young, DH ^{[1
]}

Fujimoto, TT ^{[1
]}

Tice, CM ^{[1
]}

Michelotti, EL ^{[1
]}

机构：

[1] Rohm & Haas Co, Spring House, PA 19477 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 13期

关键词：

phenylcyclohexenes; colchicine; epoxides;

D O I：

10.1016/S0040-4020(03)00216-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Colchicine mimetic (+/-)-4S,5R-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexene (1) was epoxidized to afford a mixture of epoxides. The epoxides were separately converted in two steps, with high stereoselectivity, to two regioisomeric alpha-methoxyketones. One regioisomer, (+/-)-2R,4S,5R-2-methoxy-5-nitro-4-(2,3,4-trimethoxyphenyl)cyclohexanone (17), proved to be about 12-fold more potent than synthetic precursor 1 against HCT-116 tumor cells while the other regioisomer, (+/-)-2R,4R,5S-2-methoxy-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexanone (16), and the synthetic intermediates tested showed no improvement in potency. (C) 2003 Published by Elsevier Science Ltd.

引用

页码：2223 / 2229

页数：7

共 26 条

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