Abstract
5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Indicators and Reagents
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Lactams*
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Magnetic Resonance Spectroscopy
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Methicillin Resistance*
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Microbial Sensitivity Tests
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Molecular Structure
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Staphylococcus aureus / drug effects*
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Staphylococcus aureus / genetics
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Stereoisomerism
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Structure-Activity Relationship
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beta-Lactams*
Substances
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2-((1-phenacylpyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid
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2-((pyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid
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Anti-Bacterial Agents
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Indicators and Reagents
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Lactams
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beta-Lactams