5,6-Cis-penems: broad-spectrum anti-methicillin-resistant Staphylococcus aureus beta-lactam antibiotics

J Med Chem. 1997 Jul 4;40(14):2126-32. doi: 10.1021/jm9703348.

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

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Indicators and Reagents
  • Lactams*
  • Magnetic Resonance Spectroscopy
  • Methicillin Resistance*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / genetics
  • Stereoisomerism
  • Structure-Activity Relationship
  • beta-Lactams*

Substances

  • 2-((1-phenacylpyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid
  • 2-((pyrrolidin-3-yl)thio)-6-(1-hydroxypropyl)penem-3-carboxylic acid
  • Anti-Bacterial Agents
  • Indicators and Reagents
  • Lactams
  • beta-Lactams