Discovery of isoxazolinone antibacterial agents. Nitrogen as a replacement for the stereogenic center found in oxazolidinone antibacterials

Bioorg Med Chem Lett. 2004 Sep 20;14(18):4735-9. doi: 10.1016/j.bmcl.2004.06.076.

Abstract

A series of potential antimicrobial derivatives possessing bioisosteric replacements for the central oxazolidinone ring found in oxazolidinone antibacterials have been prepared. The design concept involved replacement of the requisite sp(3)-hybridized stereogenic center found at the 5-position of the oxazolidinone with a nitrogen atom. The synthesis and antibacterial activity of three such ring systems, the benzisoxazolinones, pyrroles, and isoxazolinones is described.

Publication types

  • Comparative Study

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry*
  • Isoxazoles / pharmacology
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Nitrogen / chemistry*
  • Oxazolidinones / chemistry*
  • Oxazolone / analogs & derivatives*
  • Oxazolone / chemical synthesis
  • Oxazolone / chemistry*
  • Oxazolone / pharmacology
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Isoxazoles
  • Oxazolidinones
  • Pyrroles
  • Oxazolone
  • Nitrogen