Farnesyl and geranylgeranyl pyrophosphate analogs incorporating benzoylbenzyl ethers: Synthesis and inhibition of yeast protein farnesyltransferase

被引：32

作者：

Gaon, I ^{[1
]}

Turek, TC ^{[1
]}

Distefano, MD ^{[1
]}

机构：

[1] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(96)02066-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of two photoactive analogs (1a and 1b) of farnesyl pyrophosphate that incorporate stable ether-linked benzophenones are described. Compounds 1a and 1b were prepared from geraniol in 17% overall yield. Both 1a and 1b are competitive inhibitors of yeast protein farnesyltransferase with respect to farnesyl pyrophosphate and have K-I values of 45 nM and 49 nM. Upon photolysis for twelve hours, 1a and 1b both inactivate the enzyme by 40%. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：8833 / 8836

页数：4

共 22 条

[1]

BHALERAO UT, 1971, J AM CHEM SOC, V93, P4835

[2] PHOTOREACTIVE ANALOGS OF PRENYL DIPHOSPHATES AS INHIBITORS AND PROBES OF HUMAN PROTEIN FARNESYLTRANSFERASE AND GERANYLGERANYLTRANSFERASE TYPE-I [J].