N-Aroyl-3,5-bis(benzylidene)-4-piperidones: a novel class of antimycobacterial agents

Bioorg Med Chem. 2008 Apr 1;16(7):3602-7. doi: 10.1016/j.bmc.2008.02.009. Epub 2008 Feb 8.

Abstract

A number of 3,5-bis(benzylidene)-4-piperidones 1 and some N-4-(2-aminoethoxy)phenylcarbonyl analogs 3-6 display excellent in vitro antimycobacterial properties. In particular, 1c and 6d are potent antimycobacterials which are well tolerated in mice and are identified as important lead molecules. The nature of both the benzylidene aryl rings and the terminal basic groups which affect the antimycobacterial potencies and the absence of neurotoxic side effects were identified. Several representative compounds stimulated respiration in mitochondria isolated from rat liver and this effect was not caused by the swelling of these organelles. Various guidelines for the creation of further related novel antimycobacterial agents are provided.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / classification
  • Anti-Bacterial Agents / pharmacology*
  • Mice
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Piperidones / chemical synthesis*
  • Piperidones / chemistry
  • Piperidones / classification
  • Piperidones / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • 3,5-bis(benzylidene)-4-piperidone
  • Anti-Bacterial Agents
  • Piperidones

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