Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents.
4-(Bromomethyl) coumarins 1 have been reacted with vanillins, 2 and 2A to obtain the corresponding ethers 3 and 5. Ethers 3 have been reacted with ethyl cyanoacetate to obtain the unsaturated esters 4. Ethers 5 have been converted to the corresponding 4-(2'-benzo[b] furanyl) coumarins 6 by an intramolecular aldol condensation. Eight compounds have been screened for their anti-inflammatory activity. Out of these the 5,6-benzo-4-2'-benzo[b]furanyl) coumarin (6c) and the aryloxymethyl coumarin (4) with p-formyl group were found to be most active.
Ghate
Manjunath
M
Post Graduate Department of Studies in Chemistry, Karnatak University, 580003, Dharwad, India.
Manohar
D
D
Kulkarni
V
V
Shobha
R
R
Kattimani
S Y
SY
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D001241:Aspirin / Q000494:pharmacology; D001547:Benzaldehydes / Q000737:chemistry*; D002351:Carrageenan; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology*; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D004987:Ethers / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D006099:Granuloma / Q000139:chemically induced / Q000517:prevention & control; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010147:Pain Measurement / Q000187:drug effects; D051381:Rats; D017208:Rats, Wistar; D011930:Reaction Time / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013276:Stomach Ulcer / Q000139:chemically induced / Q000473:pathology
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001547:Benzaldehydes; D003374:Coumarins; D004987:Ethers; D007202:Indicators and Reagents; D002351:Carrageenan; C100058:vanillin; D001241:Aspirin