Synthesis and antibacterial evaluation of a novel tricyclic oxaborole-fused fluoroquinolone

Bioorg Med Chem Lett. 2013 Feb 15;23(4):963-6. doi: 10.1016/j.bmcl.2012.12.045. Epub 2012 Dec 21.

Abstract

We have designed and synthesized a novel class of compounds based on fluoroquinolone antibacterial prototype. The design concept involved the replacement of the 3-carboxylic acid in ciprofloxacin with an oxaborole-fused ring as an acid-mimicking group. The synthetic method employed in this work provides a good example of incorporating boron atom in complex molecules with multiple functional groups. The antibacterial activity of the newly synthesized compounds has been evaluated.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / pharmacology*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Ciprofloxacin / chemistry
  • Ciprofloxacin / pharmacology
  • Fluoroquinolones / chemical synthesis*
  • Fluoroquinolones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Boron Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Fluoroquinolones
  • Ciprofloxacin