Synthesis and SAR evaluation of oxadiazolopyrazines as selective Haemophilus influenzae antibacterial agents

Bioorg Med Chem Lett. 2003 Oct 6;13(19):3133-6. doi: 10.1016/s0960-894x(03)00727-3.

Abstract

The parallel synthesis and antibacterial activity of 5-hydroxy[1,2,5] oxadiazolo[3,4-b]pyrazines is reported. The compounds were synthesized by condensing diaminofurazan with alpha-keto acids to give a variety of aryl-substituted analogues. Halogenated phenyl groups at C-6 give rise to the greatest Haemophilus influenzae antibacterial activity.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Haemophilus influenzae / drug effects*
  • Haemophilus influenzae / growth & development
  • Humans
  • Microbial Sensitivity Tests / methods
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / pharmacology*
  • Pyrazines / chemical synthesis
  • Pyrazines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Oxadiazoles
  • Pyrazines