Synthesis of some novel chalcones, flavanones and flavones and evaluation of their anti-inflammatory activity

Eur J Med Chem. 2013 Jul:65:51-9. doi: 10.1016/j.ejmech.2013.04.056. Epub 2013 May 3.

Abstract

A novel series of synthetic 2'-hydroxychalcones (1a-h), 2'-methoxychalcones (2a-l), flavanones (3a-k) and flavones (4a-f) have been synthesized and evaluated for their anti-inflammatory activity in carrageenan induced rat paw oedema model. Compounds 1a, 1e-g, 2e-g, 3j, and 4f showed potent anti-inflammatory activity comparable to the reference drug indomethacin with insignificant ulceration. Compound 1f showed mild inhibition against the enzymatic activity of ovine COX-1 and COX-2 (in-vitro). Compound 1f also exhibited inhibitory activity in LPS induced TNF-α production.

Keywords: Anti-inflammatory; Chalcone; Flavanone; Flavone; Indomethacin; TNF-α.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Carrageenan
  • Cell Line
  • Chalcones / chemical synthesis
  • Chalcones / chemistry
  • Chalcones / pharmacology*
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase Inhibitors / chemical synthesis
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology*
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / drug therapy*
  • Female
  • Flavanones / chemical synthesis
  • Flavanones / chemistry
  • Flavanones / pharmacology*
  • Flavones / chemical synthesis
  • Flavones / chemistry
  • Flavones / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Male
  • Mice
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Sheep
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Chalcones
  • Cyclooxygenase Inhibitors
  • Flavanones
  • Flavones
  • Lipopolysaccharides
  • Tumor Necrosis Factor-alpha
  • Carrageenan
  • Cyclooxygenase 1
  • Cyclooxygenase 2