Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides

被引：25

作者：

Sarabia, F ^{[1
]}

Sánchez-Ruiz, A ^{[1
]}

Chammaa, S ^{[1
]}

机构：

[1] Univ Malaga, Fac Ciencias, Dept Bioquim Biol Mol & Quim Organ, E-29071 Malaga, Spain

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 05期

关键词：

E-64; CA-074; cysteine proteases inhibitors; cathepsins; sulfur ylides; epoxyamides; stereoselective synthesis;

D O I：

10.1016/j.bmc.2004.12.018

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 stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the indole of the corresponding indole epoxyamides, with various nucleophiles, we were able to prepare different epoxysuccinic acids derivatives as potential cathepsin inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1691 / 1705

页数：15

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