Preparation and biological evaluation of 5-substituted retinoic acids

被引：10

作者：

Wada, Akimori ^{[1
]}

Matsuura, Naomi ^{[1
]}

Mizuguchi, Yukari ^{[1
]}

Nakagawa, Kimie ^{[1
]}

Ito, Masayoshi ^{[1
]}

Okano, Toshio ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 18期

关键词：

retinoid receptors; retinoic acid analog; coupling reaction; vinyl nonaflate; alkenyl stannane;

D O I：

10.1016/j.bmc.2008.08.025

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：

Various 5-substituted retinoic acids were prepared by a palladium-catalyzed cross coupling reactions of vinyl nonaflates and E-or Z-3-tributylstannyl-2-beten-1-ol as a key reaction. These coupling products were then converted to the corresponding all-E-and 9Z-retinoic acid analogs via Horner -Emmons reaction and subsequent basic hydrolysis, and their biological activities were evaluated. The all-E-derivatives, 5-butyl and isobutyl analogs exhibited stronger effects for anti-proliferative and differentiation-inducing activities in HL-60 cells. In contrast, in 9Z-derivatives, none of the analogs showed any activity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：8471 / 8481

页数：11