Novel hydroxyl tricyclics (e.g., GSK966587) as potent inhibitors of bacterial type IIA topoisomerases

Bioorg Med Chem Lett. 2013 Oct 1;23(19):5437-41. doi: 10.1016/j.bmcl.2013.07.013. Epub 2013 Jul 17.

Abstract

During the course of our research to find novel mode of action antibacterials, we discovered a series of hydroxyl tricyclic compounds that showed good potency against Gram-positive and Gram-negative pathogens. These compounds inhibit bacterial type IIA topoisomerases. Herein we will discuss structure-activity relationships in this series and report advanced studies on compound 1 (GSK966587) which demonstrates good PK and in vivo efficacy properties. X-ray crystallographic studies were used to provide insight into the structural basis for the difference in antibacterial potency between enantiomers.

Keywords: Antibacterials; Bacterial type IIA topoisomerase; Hydroxyl tricyclics; In vivo efficacy; Pharmacokinetic.

MeSH terms

  • Animals
  • Bacteria / enzymology*
  • Crystallography, X-Ray
  • Dogs
  • Enzyme Activation / drug effects
  • Haplorhini
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Naphthyridines / chemistry*
  • Naphthyridines / pharmacology*
  • Rats
  • Topoisomerase II Inhibitors / chemistry*
  • Topoisomerase II Inhibitors / pharmacology*

Substances

  • GSK966587
  • Naphthyridines
  • Topoisomerase II Inhibitors