The synthesis, antibacterial, and beta-lactamase inhibitory activity of a novel asparenomycin analog. |
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Authors: | G Bouthillier H Mastalerz M Menard J Fung-Tomc E Gradelski |
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Affiliation: | Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, CT 06492-7660. |
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Abstract: | An analog, 6-(2'-hydroxyethylidene)-4 beta-methyl-1-azabicyclo[3.2.0]hept-2-ene-2- carboxylate (11), of the carbapenem beta-lactamase inhibitor, asparenomycin A, was synthesized. It possessed a spectrum of antibacterial activity that was comparable to that of asparenomycin A but was less effective as a beta-lactamase inhibitor. With ampicillin, it only exhibited a moderate level of synergy against a variety of beta-lactamase-producing organisms. Although the presence of a 4 beta-methyl group in the analog brought about a significant increase in chemical stability relative to that of asparenomycin A, it did not result in an increase in stability to kidney dehydropeptidase enzyme. |
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