N-Haloacetyl-amino-acid amides as active-site-directed inhibitors of papain and cathepsin B

C Giordano, C Gallina, V Ottaviano, V Consalvi…

文献索引：Girodano; Gallina; Ottaviano; Consalvi; Scandurra European Journal of Medicinal Chemistry, 1992 , vol. 27, # 9 p. 865 - 873

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被引用次数: 9

摘要

Abstract A series of N-haloacetyl-amino-acid amides were synthesized and tested as models of cysteine-protease inhibitors. They irreversibly inactivated papain and cathepsin B via a reversible enzyme-inhibitor intermediate. Apparent second-order rate constants of inactivation ranging from 65 to 16 700 M− 1 s− 1 were observed. Reactivity against papain, as compared to glutathione, was increased 16 400-fold for N-bromoacetyl-leucine ...