Monocyclic, substituted imidazoles as glycosidase inhibitors

被引：14

作者：

Magdolen, P ^{[1
]}

Vasella, A ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2005年 / 88卷 / 09期

关键词：

D O I：

10.1002/hlca.200590182

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A range of 4-monosubstituted and 2,4-disubstituted 1H-imidazoles and 1H-imidazole-l-ethanols (R-C(4): CH2CH2,Ph, CHOHCH2Ph, Ph, or Me; R-C(2): CH2OH, CHOHCH2OH, CN, or CH2NHAc) were prepared and tested as inhibitors of alpha and beta-glucosidases and of a P-galactosidase. A new access to 4-(2phenylethyl)-1H-imidazoles starting from 4-phenylbutan-l-ol was elaborated. The strongest inhibitors are the 2-substituted 4-(2-phenylethyl)-1H-imidazoles 24a and 26a (R-C(2): CH2OH and CHOHCHZOH) and the 2-phenylethanol 34. They inhibit the beta-galactosidase from bovine liver and the beta-glucosidase from Caldocellum saccharolyticum with inhibition constants in the micromolar range, but do not inhibit the alpha-glucosidase from brewer's yeast.

引用

页码：2454 / 2469

页数：16

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