Nucleophilic reaction of cyclopentylamine on phthalimide derivatives: synthesis and antinociceptive activity of products
Okunrobo, L.O.; Chukwuka, M.J.; Nzenwa, C.P.
Acta Poloniae Pharmaceutica 64(4): 365-368
2007
ISSN/ISBN: 0001-6837 PMID: 18536163 Document Number: 607287
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.