Synthesis and biological testings as inhibitors of HMGCoA reductase of the seco-acid of tuckolide and its C-7 epimer

被引：29
|
作者：
Colle, S
Taillefumier, C
Chapleur, Y
Liebl, R
Schmidt, A
机构：
[1] Univ Nancy 1, Grp SUCRES, UMR 7565, CNRS, F-54506 Vandoeuvre Les Nancy, France
[2] Dow AgroSci, Indianapolis, IN 46268 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 1999年 / 7卷 / 06期
关键词：
cholestereol biosynthesis; HMGCoA reductase; inhibition; tuckolide; synthesis;
D O I：
10.1016/S0968-0896(99)00020-6
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 seco-acid of the natural macrolactone, tuckolide (decarestrictin D) and the C-7 epimer have been prepared in enantiomerically pure form from D-gluconolactone and poly(3-hydroxy butyric acid). The key steps are Horner-Emmons olefination and stereoselective reduction of the resulting enone to provide both epimers at C-7. None of the seco-acids inhibit microsomal HMGCoA reductase of pea or rat liver. It may be concluded that the cholesterol biosynthesis inhibiting effect of tuckolide is unlikely to proceed via HMGCoA reductase inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1049 / 1057
页数：9
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