Synthesis and biological evaluation of new 3,5-di(trifluoromethyl)-1,2,4-triazolesulfonylurea and thiourea derivatives as antidiabetic and antimicrobial agents

Fluorinated 1,2,4-triazoles 3 and benzenesulfonyl urea and thiourea derivatives as well as their cyclic sulfonylthioureas 4–10 were prepared as antimicrobial agents. The chemistry involves the condensation of sulfanilamide derivatives 1 with trifluoroacetic anhydride to give N-di(trifluoroacetyl)sulfonamides 2 which upon reaction with hydrazine hydrate afforded the corresponding triazole derivatives 3. Reaction of triazole derivative 3a with isocyanates and isothiocyanates gave the corresponding ureas 4 and thioureas 5. Cyclization of thiourea derivatives with ethyl bromoacetate, 1,2-diiodoethane, diethyl oxalate and α-bromoacetophenone derivatives yielded the corresponding 4-oxothiazolidines 7, thiazolidines 8, 4,5-dioxothiazolidines 9 and thiazolines 10. Preliminary biological screening of the prepared compounds revealed significant antimicrobial and mild antidiabetic activities.

Graphical abstractFluorinated 1,2,4-triazoles were prepared as hypoglycemic and antibacterial agents by condensation and subsequent cyclization of the thiourea derivatives of 3,5-di(trifluoromethyl)triazoles with ethyl bromoacetate, 1,2-diiodoethane, diethyl oxalate and a-bromoacetophenone to give compounds 7–10.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights• Fluorinated triazoles and benzenesulfonyl urea, thiourea and their cyclic analogs. • Cyclization of thiourea derivatives to get thiazolidines and thiazolines. • 3-Trifluomethyltriazole derivatives show hypoglycemic and antibacterial activities.