Pyridone methylsulfone hydroxamate LpxC inhibitors for the treatment of serious gram-negative infections

J Med Chem. 2012 Feb 23;55(4):1662-70. doi: 10.1021/jm2014875. Epub 2012 Feb 8.

Abstract

The synthesis and biological activity of a new series of LpxC inhibitors represented by pyridone methylsulfone hydroxamate 2a is presented. Members of this series have improved solubility and free fraction when compared to compounds in the previously described biphenyl methylsulfone hydroxamate series, and they maintain superior Gram-negative antibacterial activity to comparator agents.

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacokinetics
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • Gram-Negative Bacteria / drug effects*
  • Gram-Negative Bacterial Infections / drug therapy*
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / pharmacokinetics
  • Hydroxamic Acids / pharmacology
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Protein Conformation
  • Pseudomonas aeruginosa / drug effects
  • Pseudomonas aeruginosa / enzymology
  • Pyridones / chemical synthesis*
  • Pyridones / pharmacokinetics
  • Pyridones / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonic Acids / chemical synthesis*
  • Sulfonic Acids / pharmacokinetics
  • Sulfonic Acids / pharmacology

Substances

  • Anti-Bacterial Agents
  • Hydroxamic Acids
  • Pyridones
  • Sulfonic Acids
  • Amidohydrolases
  • UDP-3-O-acyl-N-acetylglucosamine deacetylase

Associated data

  • PDB/3UHM