Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives

Eur J Med Chem. 2007 Feb;42(2):268-75. doi: 10.1016/j.ejmech.2006.08.004. Epub 2006 Sep 26.

Abstract

In the present investigation, a series of 5-(-4-(substituted) phenyl)-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-toluidino methane thione and 5-(substituted) phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-methoxyanilino methane thione were synthesized by the reaction between hydrazine hydrate and chalcones (3a-k) followed by condensation with appropriate aryl isothiocyanate which yielded N-substituted pyrazoline derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, compound anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1H-1-pyrazolylmethanethione (6i) was found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology

Substances

  • Aniline Compounds
  • Antitubercular Agents
  • Pyrazoles
  • anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1H-1-pyrazolylmethanethione