Synthesis and biological evaluation of new barbituric and thiobarbituric acid fluoro analogs of benzenesulfonamides as antidiabetic and antibacterial agents

A novel series of benzenesulfonamide derivatives of barbituric and thiobarbituric acids (2–12) were synthesized by condensation and cyclization reactions of various ureido and thioureido derivatives of sulfanilamides. Different substituents have been incorporated at C-5 of barbituric and thiobarbituric acid. Fluoro- and trifluoroacetyl substituents have been installed on various positions and their comparative biological screening was performed with the corresponding non-fluorinated analogs. The synthesized compounds were evaluated for their antimicrobial and antidiabetic activities. Some of the target compounds with fluorine substitution have shown very good antibacterial and antidiabetic activities.

Graphical abstractA novel series of benzenesulfonamide derivatives of barbituric and thiobarbituric acids (2–12) were synthesized. Fluoro and trifluoroacetyl substituents have been installed on various positions and their comparative biological screening was performed with the corresponding non-fluorinated analogs. Some of the target compounds have shown very good antibacterial and antidiabetic activities.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Fluoro and trifluoroacetyl derivatives of barbiturates and thiobarbiturates. ► Cyclocondensation reactions of ureido and thioureido derivatives of sulfanilamides. ► Fluoro substituted derivatives show antibacterial and hypoglycemic activities.