Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents

Fluorinated pyrazoles, and benzenesulfonylurea and thiourea derivatives as well as their cyclic sulfonylthioureas 2–18 were prepared as hypoglycemic and antibacterial agents. The chemistry involves the condensation of 4-hydrazino benzenesulfonamide hydrochloride with 1-trifluoromethyl diketones 1 to give pyrazole derivatives 2 which upon bromination gave the bromopyrazole 3. Reaction of 2 or 3 with isocyanates and isothiocyanates gave the corresponding ureas 4 and 5 and thioureas 6 and 7. Cyclization of thiourea derivatives with ethyl bromoacetate, ethyl β-bromopropionate, 1,3-dichloroacetone and α-bromoacetophenone yielded the corresponding 4-oxothiazolidines 8 and 9, 4-oxo-5,6-dihydrothiazine 10, 5-oxo-4,5-dihydrothiazines 11 and 12 and thiazolines 13 and 14. Preliminary biological screening of the prepared compounds revealed significant antidiabetic and antibacterial activities.

Fluorinated pyrazoles were prepared as hypoglycemic and antibacterial agents by condensation and subsequent cyclization of the thiourea derivatives of 3-trifluoromethylpyrazoles with ethyl bromoacetate, ethyl β-bromopropionate, 1,3-dichloroacetone and α-bromoacetophenone to give compounds 2–18.Figure optionsDownload as PowerPoint slideResearch highlights▶ Fluorinated pyrazoles and benzenesulfonylurea, thiourea and their cyclic analogs. ▶ Cyclization of thiourea derivatives to get thiazolidines and thiazines. ▶ 3-Trifluomethylpyrazole derivatives show hypoglycemic and antibacterial activities.