Enantiopure antituberculosis candidates synthesized from (-)-fenchone

Eur J Med Chem. 2014 Apr 22:77:243-7. doi: 10.1016/j.ejmech.2014.03.025. Epub 2014 Mar 12.

Abstract

The synthesis of new enantiopure N-acyl compounds derived from (-)-fenchone has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed for most of them moderate activity. The structures bearing sulfonamide functionality have comparable activity to ethambutol and possess low cytotoxicity.

Keywords: Amides; Antimycobacterial; Chiral; Fenchone; Tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Camphanes
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Ethambutol / pharmacology
  • HEK293 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Mycobacterium tuberculosis / drug effects*
  • Norbornanes / chemical synthesis
  • Norbornanes / chemistry*
  • Norbornanes / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfonamides / chemistry

Substances

  • Antitubercular Agents
  • Camphanes
  • Norbornanes
  • Sulfonamides
  • fenchone
  • Ethambutol