Synthesis and antimycobacterial activity of N'-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide derivatives

Eur J Med Chem. 2009 Dec;44(12):4954-9. doi: 10.1016/j.ejmech.2009.08.009. Epub 2009 Sep 1.

Abstract

The present article describes a series of twenty-six N'-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide (4-29), which were synthesized and evaluated for their cell viabilities in non infected and infected macrophages with Mycobacterium bovis Bacillus Calmette-Guerin (BCG). Afterwards, the non-cytotoxic compounds (4, 6, 8, 15, 21, 23, 24, 27 and 28) were assessed against Mycobacterium tuberculosis ATCC 27294 using the micro plate Alamar Blue assay (MABA) and the activity expressed as the minimum inhibitory concentration (MIC) in microg/mL. The compounds 6, 23, 27 and 28 exhibited a significant activity (50-100 microg/mL) when compared with first line drugs such as pyrazinamide and were not cytotoxic in their respective MIC values.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / pharmacology
  • Antitubercular Agents* / chemical synthesis
  • Antitubercular Agents* / pharmacology
  • Benzylidene Compounds / chemical synthesis*
  • Benzylidene Compounds / chemistry
  • Benzylidene Compounds / pharmacology
  • Cell Survival
  • Drug Design
  • Humans
  • Hydrazines / chemical synthesis*
  • Hydrazines / chemistry
  • Hydrazines / pharmacology
  • Macrophages / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Pyrazinamide / chemical synthesis*
  • Pyrazinamide / chemistry
  • Pyrazinamide / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antitubercular Agents
  • Benzylidene Compounds
  • Hydrazines
  • Pyrazinamide
  • carbohydrazide