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Synthesis of 5‐Phenyl‐1‐(3‐pyridyl)‐1 H ‐1,2,4‐triazole‐3‐carboxylic Acid Derivatives of Potential Anti‐inflammatory Activity
Author(s) -
Rabea Safwat M.,
ElKoussi Nawal A.,
Hassan Hoda Y.,
AboulFadl Tarek
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500151
Subject(s) - chemistry , semicarbazide , carboxylic acid , hydrazide , hydrochloride , 1,2,4 triazole , hydroxamic acid , isothiocyanate , triazole , phenyl isothiocyanate , medicinal chemistry , pyrazole , proton nmr , stereochemistry , organic chemistry
A series of 5‐phenyl‐1‐(3‐pyridyl)‐1 H ‐1,2,4‐triazole‐3‐carboxylic acid derivatives 4 – 10 were synthesized by rearrangement of 4‐(3‐pyridyl)‐hydrazono‐2‐phenyl‐2‐oxazolin‐5‐one 3 in the presence of different nucleophiles to afford derivatives 4 , 7 , and 8 , while hydroxamic acid derivative 6 was prepared from reaction of methyl ester 4 with hydroxylamine hydrochloride. Semicarbazide 9 and thiosemicarbazide 10 , derivatives of the 5‐phenyl‐1‐(3‐pyridyl)‐1 H ‐1,2,4‐triazole‐3‐carboxylic acid, were synthesized via hydrazide 8 with potassium cyanate and appropriate isothiocyanate, respectively. The structures of the synthesized compounds were confirmed by elemental analyses, IR, 1 H‐NMR, and mass spectra. The results of the anti‐inflammatory activity of the synthesized derivatives showed that most of the tested compounds 4 – 10 showed significant inhibition against carrageenan‐induced rat paw edema in albino rats. Derivatives 4 and 8 showed promising results and were found to be equipotent or more potent than Indomethacin and Celecoxib as reference drugs at two dose levels, 5 and 10 mg/kg, and they have no ulcerogenic activity.