Synthesis of 6-aminomethyl derivatives of benzopyran-4-one with dual biological properties: anti-inflammatory-analgesic and antimicrobial

Eur J Med Chem. 2009 Dec;44(12):4896-903. doi: 10.1016/j.ejmech.2009.08.001. Epub 2009 Aug 6.

Abstract

A series of 6-aminomethyl-2-aryl-1-benzopyran-4-one derivatives (10-24) were synthesized. The compounds were tested for anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation actions. Among the tested compounds, six compounds 11, 13, 16, 18, 21 and 23 showed higher degree of anti-inflammatory activity (>75% activity of standard drug ibuprofen). In addition to remarkable anti-inflammatory activity, analgesic activity was found to be comparable with that of the standard drug ibuprofen. Compounds 16 and 21 showed a significant GI protection (with respect to ulcerogenesis) and a marked decrease in lipid peroxidation values whereas compounds 11 and 16 were found to possess antimicrobial activity against Staphylococcus aureus, Escherichia coli, Rhizopus oryza and Penicillum citrum with an MIC of 10 microg/mL.

MeSH terms

  • Amination
  • Analgesics / chemical synthesis*
  • Analgesics / chemistry
  • Analgesics / pharmacology
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Bacteria / drug effects*
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Flavones / chemical synthesis
  • Flavones / chemistry
  • Flavones / pharmacology
  • Fungi / drug effects*
  • Lipid Peroxidation / drug effects
  • Methylation
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Analgesics
  • Anti-Infective Agents
  • Anti-Inflammatory Agents
  • Benzopyrans
  • Flavones