Synthesis of N-substituted indole-2-carboxamides and investigation of their biochemical responses against free radicals

J Enzyme Inhib Med Chem. 2007 Jun;22(3):319-25. doi: 10.1080/14756360601114742.

Abstract

The antioxidant role of novel N-substituted indole-2-carboxamides (I2CDs) was investigated for their inhibitory effects on superoxide anion (O2-) and lipid peroxidation (LP). Among the synthesized I2CDs, 3, 4, 6, 8 and 9 significantly inhibited O2*- with an inhibition range at 70-98%. Examination of substituent effects on activity showed that both the ortho- and para- positions of the benzamide residue needs to be dichlorinated in order to get a maximum inhibitory effect on superoxide anion. In general, halogenated derivatives were found more active then the non-halogenated ones. However, none of the I2CDs had a significant inhibitory effects on the level of lipid peroxidation; only compounds 7 and 10 moderately decreased LP levels by over 50% at 10(-3) M concentrations.

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Drug Evaluation, Preclinical
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • In Vitro Techniques
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Lipid Peroxidation / drug effects
  • Liver / drug effects
  • Liver / metabolism
  • Magnetic Resonance Spectroscopy
  • Male
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Superoxides / metabolism

Substances

  • Antioxidants
  • Free Radical Scavengers
  • Indoles
  • Superoxides