Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues.
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.
Nicolaides
Demetrios N
DN
Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece. nicol@chem.auth.gr
Gautam
Daman R
DR
Litinas
Konstantinos E
KE
Hadjipavlou-Litina
Dimitra J
DJ
Fylaktakidou
Konstantina C
KC
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D000975:Antioxidants / Q000138:chemical synthesis* / Q000627:therapeutic use; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D007783:Lactones / Q000138:chemical synthesis* / Q000627:therapeutic use; D008956:Models, Chemical; D051381:Rats; D013329:Structure-Activity Relationship
D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D002351:Carrageenan