Regioselective reaction: synthesis and pharmacological study of Mannich bases containing ibuprofen moiety.
A series of 4-[(4-aryl)methylidene]amino-2-(substituted-4-ylmethyl)-5-{1-[4-(2-methylpropyl)phenyl]ethyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione (6) were synthesized from an arylpropionic acid namely, ibuprofen by a three-component Mannich reaction. Aminomethylation of 4-[(4-aryl)methylidene]amino-5-{1-[4-(2-methylpropyl)phenyl] ethyl}-4H-1,2,4-triazole-3-thiol (5) with formaldehyde and a secondary amine furnished this novel series of Mannich bases (6). Both Schiff bases (5) and Mannich bases (6) were well characterized on the basis of IR, NMR, mass spectral data and elemental analysis. They were screened for their anti-inflammatory, analgesic, antibacterial and antifungal activities. Some of the Mannich bases (6) carrying morpholino and N-methylpiperazino residues were found to be promising anti-inflammatory and analgesic agents.
Sujith
K V
KV
Department of Studies in Chemistry, Mangalore University, Mangalagangothri 574199, Karnataka, India.
Rao
Jyothi N
JN
Shetty
Prashanth
P
Kalluraya
Balakrishna
B
D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001230:Aspergillus / Q000187:drug effects; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D004926:Escherichia coli / Q000187:drug effects; D007052:Ibuprofen / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy; D008352:Mannich Bases / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D010146:Pain / Q000188:drug therapy; D051381:Rats; D017208:Rats, Wistar; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D018712:Analgesics, Non-Narcotic; D000894:Anti-Inflammatory Agents, Non-Steroidal; D008352:Mannich Bases; D012545:Schiff Bases; D014230:Triazoles; C045575:1,2,4-triazole; D007052:Ibuprofen