Nucleophilic reaction of cyclopentylamine on phthalimide derivatives: synthesis and antinociceptive activity of products.
The reaction of cyclopentylamine with N-prop-2-ynylphthalimde la and 4-phthalimidobutyric acid 1b was carried out in dimethylformamide at room temperature to afford benzamido-N-prop-2-ynyl-N-cyclopentyl -carboxamide (3) and benzamido-N,N-bis (cyclopentyl)-carboxamide (4), respectively. IR, NMR, and microanalyses were used to unequivocally characterize the compounds obtained. The new compounds were evaluated pharmacologically for their in vivo antinociceptive activity using acetic acid-induced writhing assay and compound 3 had significant activity (70%) comparable to indomethacin (71%) but better than acetylsalicylic acid (59%), however, compound 4 had lower activity (29%). The effects were dose-dependent.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, Nigeria. bricyedo@yahoo.com
Lucky O
LO
Okunrobo
Madu J
MJ
Chukwuka
Chisom P
CP
Nzenwa
D019342:Acetic Acid; D000700:Analgesics / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D001241:Aspirin / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D005260:Female; D007213:Indomethacin / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D010146:Pain / Q000188:drug therapy*; D010147:Pain Measurement; D010795:Phthalic Acids / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared
D000700:Analgesics; D010795:Phthalic Acids; C529787:benzamido-N,N-bis(cyclopentyl)carboxamide; C529786:benzamido-N-prop-2-ynyl-N-cyclopentylcarboxamide; D019342:Acetic Acid; D001241:Aspirin; D007213:Indomethacin