Preparation and antidiabetic activity of some sulfonylurea derivatives of 3,5-disubstituted pyrazoles

Abstract

Four series of p-[3,5-dimethyl- (and 5-methyl-3-carboxy-) pyrazole-1]benzenesulfonylureas, thioureas, 2-thiohydantions, and 5,6-dihydro-4(3H)-oxo-2(1H)-pyrimidinethiones were prepared for evaluation as hypoglycemic agents. Biological testing of these compounds showed that some possessed antidiabetic activity.

Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and <i>in Vitro</i> Studies

“…The starting intermediates 1-(4-substitutedphenyl)-3-methyl-1H-pyrazol-5(4H)-ones 2a and 2c were synthesized by reacting the commercially available 4-chlorophenylhydrazine hydrochloride 1a or the synthesized 4-hydrazinylbenzenesulfonamide hydrochloride 1b 25) with ethyl acetoacetate in acetic acid in the presence of sodium acetate to obtain 2a [26][27][28] or in refluxing methanol to obtain 2c. 29,30) Methylation of 2a and 2c with dimethylsulfate (DMS) in alkaline medium afforded the N-methyl derivatives 3a 31) and 3d.…”

“…All the reactions were followed by TLC using silica gel F254 plates (Merck), using chloroform: methanol 9 : 1 or chloroform as eluting system and were visualized by UV-lamp. Compounds 1b, 25) and 3a 31) were prepared according to reported methods, while compounds 8a, 36) 8b, 46) 2a, [26][27][28] 2c, 29,30) 2b, [33][34][35] and 3d 32) were prepared according to modified procedures from the reported methods.…”

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,5-diarylpyrazole derivatives

“…Cyclocondensation of the appropriate enaminone (8a-d) with 4-hydrazinylbenzenesulfonamide hydrochloride (9a) 22 , methanesulfonylphenylhydrazine hydrochloride (9b) 23,24 or 4-hydrazinobenzoic acid (9c) 25 in aqueous ethanol afforded the respective 1,5-diarylpyrazoles (10a-l) in good yields (56-88%) (Scheme 1). …”

“…Silica gel column chromatography was performed using Merck silica gel 60 ASTM (70-230 mesh). Compounds 8a-d [15][16][17][18][19][20][21] , 9a-c [22][23][24][25] were prepared according to the reported procedures.…”

Preparation and Antidiabetic Activity of New Substituted 3,5-Diarylpyrazolesulfonylurea Derivatives

“…Since several 3,5-dimethylpyrazoles possess hypoglycemic activities as great as 100 times that of tolbutamide in glucose-primed intact rats (1)(2)(3)(4)(5), studies have been conducted on the synthesis of new 3,5-disubstituted pyrazoles (6)(7)(8)(9). In continuation of previous work (8,9), many new substituted 3,5-diarylpyrazolesulfonylurea derivatives were prepared'.…”