New 3- and 4-hydroxyfuranones as anti-oxidants and anti-inflammatory agents

Bioorg Med Chem. 2005 Jul 15;13(14):4552-64. doi: 10.1016/j.bmc.2005.04.055.

Abstract

Two series of new furanones substituted by methylsulfonylphenyl or methylsulfamidophenyl moieties were found to protect against oxidation damage by inhibiting or quenching free radicals and reactive oxygen species in in vitro experiments. The effect on lipid peroxidation was also examined. In addition, we investigated the activity of products in two models of inflammation: phorbol ester-induced ear edema in mice and carrageenan-induced paw edema in rat. The most powerful compounds and with reducing activity against DPPH (IC50=1779 and 57 microM, respectively), superoxide anion quenching capacity (IC50=511 and 49 microM, respectively), lipid peroxidation inhibitory effect and anti-inflammatory properties (about 50-65% inhibition of edema at 200 mg/kg ip in both tests used) were selected for further pharmacological and toxicological tests because of their attractive profile for the treatment of inflammatory diseases.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Anti-Inflammatory Agents / therapeutic use
  • Antioxidants / pharmacology*
  • Antioxidants / therapeutic use
  • Carrageenan / adverse effects
  • Edema / drug therapy
  • Furans / pharmacology*
  • Furans / therapeutic use
  • Magnetic Resonance Spectroscopy
  • Mice
  • Rats
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Tetradecanoylphorbol Acetate / adverse effects

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Furans
  • Carrageenan
  • Tetradecanoylphorbol Acetate