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Enantioselective Synthesis and Profiling of Two Novel Diazabicyclooctanone ?-Lactamase Inhibitors.

ABSTRACT: The enantioselective synthesis of two novel cyclopropane-fused diazabicyclooctanones is reported here. Starting from butadiene monoxide, the key enone intermediate 7 was prepared in six steps. Subsequent stereoselective introduction of the cyclopropane group and further transformation led to compounds 1a and 1b as their corresponding sodium salt. The great disparity regarding their hydrolytic stability was rationalized by the steric interaction between the cyclopropyl methylene and urea carbonyl. These two novel ?-lactamase inhibitors were active against class A, C, and D enzymes.

SUBMITTER: Xiong H

PROVIDER: S-EPMC4190641 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis and Profiling of Two Novel Diazabicyclooctanone β-Lactamase Inhibitors.

Xiong Hui H Chen Brendan B Durand-Réville Thomas F TF Joubran Camil C Alelyunas Yun W YW Wu Dedong D Huynh Hoan H

ACS medicinal chemistry letters 20140812 10

The enantioselective synthesis of two novel cyclopropane-fused diazabicyclooctanones is reported here. Starting from butadiene monoxide, the key enone intermediate 7 was prepared in six steps. Subsequent stereoselective introduction of the cyclopropane group and further transformation led to compounds 1a and 1b as their corresponding sodium salt. The great disparity regarding their hydrolytic stability was rationalized by the steric interaction between the cyclopropyl methylene and urea carbonyl ...[more]

PMID: 25313328

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