Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues

Eur J Med Chem. 2004 Apr;39(4):323-32. doi: 10.1016/j.ejmech.2004.01.003.

Abstract

Treatment of 3-hydroxy-beta-lapachone 4 with ylide 5 gave the coumarin derivative 7a, which was transformed to compounds 10-14. Compound 14 was then transformed to benzo[f]seselin 15 as well as to benzo[l]khellactones 16, 18 from which the title compounds 17, 19(I), 19(II), 20, 21(I) and 21(II) were prepared. All the tested compounds were found to interact with DPPH in a concentration and time dependent manner. All the tested compounds highly inhibited the soybean lipoxygenase, whereas compounds 12, 17 and 19(II) highly compete with DMSO for (*)OH. Compounds 7a, 7b, 12 and 17 induced at 48.7-58.9% protection against carrageenin induced rat paw edema.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / therapeutic use
  • Antioxidants / chemical synthesis*
  • Antioxidants / therapeutic use
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Carrageenan
  • Edema / chemically induced
  • Edema / drug therapy*
  • Lactones / chemical synthesis*
  • Lactones / therapeutic use
  • Models, Chemical
  • Rats
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Bridged Bicyclo Compounds, Heterocyclic
  • Lactones
  • Carrageenan