The Bsmoc group as a novel scaffold for the design of irreversible inhibitors of cysteine proteases

Iley, J; Moreira, R; Martins, L; Guedes, RC; Soares, CM

http://hdl.handle.net/10451/21500

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Resumo(s)

Carbamate and ester derivatives of the 1,1-dioxobenzo[b]thiophen-2-ylmethyloxycarbonyl (Bsmoc) scaffold react readily with thiols via a Michael addition at rates not significantly affected by the nature of the carboxylic or carbamic acid leaving group. These Michael acceptors are irreversible inhibitors of the cysteine proteases papain and human liver cathepsin B, displaying first-order kinetics with respect to inhibitor concentration. In contrast, none of the Bsmoc derivatives inhibited porcine pancreatic elastase, a serine protease. (C) 2006 Elsevier Ltd. All rights reserved.

Palavras-chave

Chemistry, Medicinal Chemistry, Organic

URI

http://hdl.handle.net/10451/21500

Citação

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - Vol. 16, n. 10 (MAY 15 2006), p. 2738-2741

Editora

PERGAMON-ELSEVIER SCIENCE LTD

DOI

http://dx.doi.org/10.1016/j.bmcl.2006.02.007

Coleções

FF - Produção Científica 2000-2009

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