Article ID Journal Published Year Pages File Type
1314225 Journal of Fluorine Chemistry 2011 7 Pages PDF
Abstract

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.

Graphical abstractFluorinated 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 full-size imageDownload 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.

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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