SYNTHESES AND ANTI-INFLAMMATORY ACTIONS OF 4,5,6,7-TETRAHYDROINDAZOLE-5-CARBOXYLIC ACIDS

A novel series of 1-aryl-4, 5, 6, 7-tetrahydro-1 H-indazole-5-carboxylic acids and 2-aryl-4, 5, 6, 7-tetrahydro-2H-indazole-5-carboxylic acids were synthesized via condensation between a phenylhvdrazine and a 2-(hydroxymethylene)cyclohexanone-4-carboxylate. and the antiinflammatory activity was determined. In the carrageenan edema test. l-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. © 1979, American Chemical Society. All rights reserved.