Antimycobacterial activity generated by the amide coupling of (-)-fenchone derived aminoalcohol with cinnamic acids and analogues

Bioorg Med Chem Lett. 2014 Nov 1;24(21):5030-3. doi: 10.1016/j.bmcl.2014.09.021. Epub 2014 Sep 16.

Abstract

Aminoethyl substituted 2-endo-fenchol prepared from (-)-fenchone was used as scaffold for the synthesis of series of 31 amide structures by N-acylation applying cinnamic acids and analogues. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed for some of them promising activity-up to 0.2 μg/ml, combined with relatively low cytotoxicity of the selected active compounds.

Keywords: Amides; Cinnamic acids; Fenchone; Tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Amides / chemistry*
  • Amino Alcohols / chemistry*
  • Antitubercular Agents / chemistry*
  • Antitubercular Agents / pharmacology
  • Antitubercular Agents / toxicity
  • Camphanes
  • Cell Survival / drug effects
  • Cinnamates / chemistry*
  • HEK293 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects
  • Norbornanes / chemistry*
  • Norbornanes / pharmacology
  • Norbornanes / toxicity
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Amides
  • Amino Alcohols
  • Antitubercular Agents
  • Camphanes
  • Cinnamates
  • Norbornanes
  • fenchone
  • cinnamic acid