STUDIES ON CEPHEM SULFONES AS MECHANISM-BASED INACTIVATORS OF HUMAN-LEUKOCYTE ELASTASE .3. REACTIONS ENSUING FROM CHEMICAL BETA-LACTAM CLEAVAGE

被引：9

作者：

ALPEGIANI, M

BISSOLINO, P

BORGHI, D

RIZZO, V

PERRONE, E

机构：

[1] Farmitalia Carlo Erba R and D, 20014 Nerviano, MI

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(01)80936-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The molecular events ensuing from beta-lactam cleavage of cephem sulfones by chemical nucleophiles have been determined. Alkaline hydrolysis and methanolysis led to opening of the dihydrothiazine ring to produce sulfinate salts. Cleavages promoted by NaN3, imidazole and n-PrSH in MeCN gave products from dihydrothiazine opening and desulfonylation. By contrast with enzyme-promoted reactions, expulsion of potential leaving groups at C3' was not observed.

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页码：2259 / 2264

页数：6

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