Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents.
Eight novel 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles (3a-h) have been synthesized in order to obtain new compounds with potential anti-nociceptive and anti-inflammatory activity. The titled compounds were synthesized by the condensation of 1-[2-(1H-tetrazol-5-yl) ethyl]-1H-benzotriazole (2) and appropriate acid chlorides. Compound 2 was synthesized by reacting 3-(1H-benzo[d][1,2,3]triazol-1-yl)propanonitrile (1) with sodium azide and ammonium chloride in the presence of dimethylformamide. The synthesized compounds were characterized by spectroscopic methods (IR, 1H NMR, mass spectroscopy) and elemental analysis. The titled compounds were evaluated for anti-nociceptive activity by the hot plate method and the writhing response method, and anti-inflammatory activity was evaluated by the carragenean induced paw edema method. 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone (3d) and 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-hydroxyphenyl)methanone (3g) exhibited significant anti-nociceptive activity. 1-(2-(1-Tosyl-1H-tetrazol-5-yl)ethyl)-1H-benzo[d][1,2,3]triazole (3c) and 4,5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl sulfonyl)benzenamine (3f) elicited superior anti-inflammatory activity compared to other synthesized compounds. Further investigations are needed to discern the mechanism of action.
Rajasekaran
Aiyalu
A
KMCH College of Pharmacy, Coimbatore, Tamilnadu, India. rsekaran2001in@yahoo.co.in
Rajagopal
Kalasalingam Ananda
KA
D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D055808:Drug Discovery / Q000379:methods*; D004487:Edema / Q000188:drug therapy / Q000473:pathology; D007274:Injections, Intraperitoneal; D051379:Mice; D019906:Nuclear Magnetic Resonance, Biomolecular; D010147:Pain Measurement / Q000187:drug effects / Q000379:methods; D013055:Spectrophotometry, Infrared; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity
D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D014230:Triazoles; C012771:benzotriazole