Syntheses and antiinflammatory actions of 4,5,6,7-tetrahydroindazole-5-carboxylic acids

Abstract

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.

HETEROAROMATIZATION WITH SULFONAMIDO PHENYL ETHANONE: PART (IV). SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW N-ETHYL-N-METHYLBENZENESULFONAMIDE, 1,3,4-THIADIAZOLE, 1,3,4-THIADIAZINE, 4-OXOTHIAZOLIDINE AND PYRAZOLO[5,1-c][1,2,4]TRIAZINE DERIVATIVES

“…IR spectrum of 11 showed absorption bands at 3169 cm -1 for NH group and 2262 cm -1 for CN group, while 1 H NMR spectrum of 11 showed singlet at δ 2.29 ppm for CH3-C=N, singlet at δ 4.26 ppm for CH2CN and singlet at δ 11.18 ppm for NH group. Interaction of hydrazonecarbodithioate derivative 7 with hydrazonoyl bromides 12a,b [28][29][30] in ethanol containing triethylamine gave the corresponding 1,3,4-thidiazole derivatives 15a,b, respectively. The formation of 15a,b can be rationalized via elimination of methylmercaptan from the corresponding cyclo adduct intermediates 14a,b, which is assumed to be formed from 1,3-dipolar cyclo addition of nitrileimines to the thiocarbonyl double bond.…”

Indazole: a medicinally important heterocyclic moiety

“…In the carrageenan edema test, 1-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid (15) was found to be the most active compound (Nagakura et al, 1979).…”

Catalysis by Amberlyst A-21: A Greener Approach to 4,5,6,7-Tetrahydro-1H-indazol-3(2H)-ones via Construction of Cyclohexanones

“…Additionally, evaluation of a series of 1-aryl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acidsfor their anti-inflammatory activities led to the identification of 1-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid (B, Fig. 1) that showed high activities in vivo with ED 50 value of 3.5 mg/kg in the carrageenan edema test, [9] Similarly, 2-methyl-3-methylamino-4,5,6,7-tetrahydroindazole (C, Fig. 1) has showed anti-inflammatory and analgesic activities.…”