Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized

Bioorg Med Chem. 2006 Nov 1;14(21):7113-20. doi: 10.1016/j.bmc.2006.06.068. Epub 2006 Aug 2.

Abstract

Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS(-), *OH and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization.

MeSH terms

  • Analgesics / pharmacology*
  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / pharmacology*
  • Calorimetry, Differential Scanning
  • Cyclooxygenase Inhibitors / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Female
  • Free Radicals / chemistry
  • Lipoxygenase Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Ninhydrin / chemistry
  • Ninhydrin / pharmacology*
  • Phenol / chemistry
  • Phenol / pharmacology*
  • Rats
  • Rats, Wistar
  • Spectrophotometry, Infrared

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Antioxidants
  • Cyclooxygenase Inhibitors
  • Free Radicals
  • Lipoxygenase Inhibitors
  • Phenol
  • Ninhydrin