COMPARATIVE REACTIVITY OF 1-CARBA-1-DETHIACEPHALOSPORINS WITH CEPHALOSPORINS

被引：51

作者：

BLASZCZAK, LC ^{[1
]}

BROWN, RF ^{[1
]}

COOK, GK ^{[1
]}

HORNBACK, WJ ^{[1
]}

HOYING, RC ^{[1
]}

INDELICATO, JM ^{[1
]}

JORDAN, CL ^{[1
]}

KATNER, AS ^{[1
]}

KINNICK, MD ^{[1
]}

MCDONALD, JH ^{[1
]}

MORIN, JM ^{[1
]}

MUNROE, JE ^{[1
]}

PASINI, CE ^{[1
]}

机构：

[1] ELI LILLY INT CORP,LILLY RES LAB,LILLY CORP CTR,INDIANAPOLIS,IN 46285

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1990年 / 33卷 / 06期

关键词：

D O I：

10.1021/jm00168a019

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, β-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the β-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type. © 1990, American Chemical Society. All rights reserved.

引用

页码：1656 / 1662

页数：7

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