THE SYNTHESIS, ANTIBACTERIAL, AND β-LACTAMASE INHIBITORY ACTIVITY OF A NOVEL ASPARENOMYCIN ANALOG

An analog, 6-(2'-hydroxyethylidene)-4β-methyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (11), of the carbapenem β-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...

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Bibliographic Details
Published in:Journal of antibiotics 1992/02/25, Vol.45(2), pp.240-245
Main Authors: BOUTHILLIER, GILLES, MASTALERZ, HAROLD, MENARD, MARCEL, FUNG-TOMC, JOAN, GRADELSKI, ELIZABETH
Format: Article
Language:English
Subjects:
Ampicillin - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Clavulanic Acids - pharmacology
Drug Synergism
Medical sciences
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Thienamycins - chemical synthesis
Thienamycins - chemistry
Thienamycins - pharmacology
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Summary:An analog, 6-(2'-hydroxyethylidene)-4β-methyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (11), of the carbapenem β-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 β-lactamase inhibitor. With ampicillin, it only exhibited a moderate level of synergy against a variety of β-actamase-producing organisms. Although the presence of a 4β-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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.45.240