Syntheses and antiinflammatory actions of 4,5,6,7-tetrahydroindazole-5-carboxylic acids.
A novel series of 1-aryl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acids and 2-aryl-4,5,6,7-tetrahydro-2H-indazole-5-carboxylic acids were synthesized via condensation between a phenylhydrazine and a 2-(hydroxymethylene)cyclohexanone-4-carboxylate, and the antiinflammatory activity was determined. In the carrageenan edema test, 1-aryl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acids exhibited fairly high antiinflammatory activity. However, the 2-aryl isomers were far less active than the former. The most active compound of the series was 1-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid, which had an ED50 value of 3.5 mg/kg.
D000700:Analgesics / Q000138:chemical synthesis; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D001169:Arthritis, Experimental / Q000503:physiopathology; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000503:physiopathology; D007191:Indazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D011720:Pyrazoles / Q000138:chemical synthesis*; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced; D013329:Structure-Activity Relationship
D000700:Analgesics; D000893:Anti-Inflammatory Agents; D007191:Indazoles; D011720:Pyrazoles; D002351:Carrageenan