Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents

Arch Pharm Res. 2012 Jun;35(6):995-1002. doi: 10.1007/s12272-012-0606-9. Epub 2012 Jun 30.

Abstract

A series of novel 5-aryl-3-cyclopropyl-4,5-dihydropyrazole derivatives 2a-p were synthesized via cyclization of chalcones 1a-h with thiosemicarbazide or semicarbazide HCl and evaluated as anti-inflammatory/antioxidant agents. The structures were confirmed by elemental analyses and spectral data. The free radical scavenging activity toward superoxide was determined. Their effect on hepatocytes viability and nitric oxide (NO) production in LPS-stimulated macrophages was also determined. The results showed that compounds 2e and 2n demonstrated the highest free-radical scavenging and anti-inflammatory activities, thus can be useful in the prevention of oxidative stress and inflammation-related disorders.

MeSH terms

  • Animals
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Cell Survival / drug effects
  • Cells, Cultured
  • Dose-Response Relationship, Drug
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / pharmacology*
  • Hepatocytes / drug effects
  • Hepatocytes / pathology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology*
  • Spectrophotometry, Infrared
  • Superoxides / chemistry

Substances

  • Anti-Infective Agents
  • Free Radical Scavengers
  • Lipopolysaccharides
  • Pyrazoles
  • Superoxides
  • Nitric Oxide