Application of Virtual Screening to the Identification of New LpxC Inhibitor Chemotypes, Oxazolidinone and Isoxazoline

J Med Chem. 2018 Oct 25;61(20):9360-9370. doi: 10.1021/acs.jmedchem.8b01287. Epub 2018 Oct 3.

Abstract

This report summarizes the identification and synthesis of novel LpxC inhibitors aided by computational methods that leveraged numerous crystal structures. This effort led to the identification of oxazolidinone and isoxazoline inhibitors with potent in vitro activity against P. aeruginosa and other Gram-negative bacteria. Representative compound 13f demonstrated efficacy against P. aeruginosa in a mouse neutropenic thigh infection model. The antibacterial activity against K. pneumoniae could be potentiated by Gram-positive antibiotics rifampicin (RIF) and vancomycin (VAN) in both in vitro and in vivo models.

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Isoxazoles / chemistry*
  • Isoxazoles / pharmacology*
  • Mice
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Oxazolidinones / chemistry*
  • Oxazolidinones / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Enzyme Inhibitors
  • Isoxazoles
  • Oxazolidinones
  • Amidohydrolases
  • LpxC deacetylase, Pseudomonas