Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I

被引：11

作者：

Makabe, H

Kimura, Y

Higuchi, M

Konno, H

Murai, M

Miyoshi, H

机构：

[1] Shinshu Univ, Grad Sch Agr, Nagano 3994598, Japan

[2] Kyoto Prefectural Univ Med, Grad Sch Med Sci, Dept Chem, Kita Ku, Kyoto 6038334, Japan

[3] Kyoto Univ, Grad Sch Agr, Div Appl Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 09期

基金：

日本学术振兴会;

关键词：

annonaceous acetogenin; antitumor; mitochondrial complex I; stereoselective synthesis;

D O I：

10.1016/j.bmc.2005.12.015

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 convergent stereoselective Synthesis of (4R, 15R, 16R, 21S)- and (4R, 15S, 16S, 21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds wits examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed it remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. Our results indicate that to maintain potent inhibitory effect, the hydroxylated lactone cannot substitute for the hydroxylated mono- or bis-THF rings with it long alkyl chain that can be seen in ordinary acetogenins. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3119 / 3130

页数：12

共 29 条

[1] Dynamic function of the alkyl spacer of acetogenins in their inhibitory action with mitochondrial complex I (NADH-ubiquinone oxidoreductase) [J].