Ring opening of 1-phthaloylimido-[4-(2-methoxyphenyl) piperazin-1-yl]alkyl derivatives: synthesis, analgesic and anti-inflammatory properties of products.
Phthaloylimidoalkyl derivatives (1a, 1b) were treated with isopropylamine to give 3-benzamido-1-(4-(2-methoxyphenyl)piperazin-1-yl)]propyl-2-isopropyl carboxamide (3a) and 4-benzamido-1-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-2-isopropyl carboxamide (3b). The compounds were unequivocally characterized by IR, NMR and MS spectra and elemental analysis. Carrageenan-induced rat paw assay was used to screen 3a and 3b for anti-inflammatory activity. 3b significantly (p <0.001) inhibited the inflammation caused by carrageenan after 3 h compared to 3a and indomethacin. Mouse writhing assay was performed to evaluate 3a and 3b. It revealed that 3b (10 mg/kg) produced 71% inhibition when compared to 3a (40 mg/kg) and acetylsalicylic acid (100 mg/kg). The results show that the length of the alkyl chain that separates the terminal nitrogen atom from the phthalic acid moiety also affects the activity of 3a and 3b in a dose dependent manner.
Okunrobo
Lucky O
LO
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, Nigeria. bricyedo@yahoo.com
Usifoh
Cyril O
CO
D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D005260:Female; D008297:Male; D051379:Mice; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship
C547703:3-benzamido-1-(4-(2-methoxyphenyl)piperazin-1-yl)propyl-2-isopropyl carboxamide; C547704:4-benzamido-1-(4-(2-methoxyphenyl)piperazin-1-yl)butyl-2-isopropyl carboxamide; D018712:Analgesics, Non-Narcotic; D000893:Anti-Inflammatory Agents; D001549:Benzamides; D010879:Piperazines