Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
A series of (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates has been prepared and screened for analgesic and antiinflammatory properties in mice and rats. The tabulated results reveal several 2-(4-substituted phenyl-1-piperazinyl)ethyl 2-(7- or 8-substituted 4-quinolinylamino)benzoates to be six to nine times more potent analgesics than the reference compounds (glafenine and aminopyrine) and to possess minor antinflammatory activity. Compound 45, 2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl 2-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoate (antrafenine), showed marked analgesic activity, long duration of action, and excellent tolerance in pharmacological and toxicological studies, as well as in clinical trials.
D000085:Acetates / Q000037:antagonists & inhibitors; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D002351:Carrageenan; D004487:Edema / Q000503:physiopathology; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D009539:Nicotinic Acids / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
D000085:Acetates; D062365:Aminobenzoates; D000700:Analgesics; D000893:Anti-Inflammatory Agents; D009539:Nicotinic Acids; D002351:Carrageenan