Synthesis and biological evaluation of some new pyrazoline substituted benzenesulfonylurea/thiourea derivatives as anti-hyperglycaemic agents and aldose reductase inhibitors

•Seventeen new pyrazoline substituted benzenesulfonylurea/thiourea derivatives (2a–q) were synthesized.•Thirteen compounds showed moderate to good anti-hyperglycaemic activity.•Compounds 2g and 2m showed anti-hyperglycaemic activity comparable to the standard drug gliclazide.•Six compounds (2h, 2k, 2l, 2n, 2o and 2q) were found more effective ARIs than the known ARI sorbinil.•Five compounds (2h, 2k, 2l, 2n and 2o) showed dual action (anti-hyperglycaemic and aldose reductase inhibition).

Seventeen new pyrazoline substituted benzenesulfonylurea/thiourea derivatives (2a–q) were synthesized and characterized by elemental analysis and various spectroscopic techniques viz; IR, 1H NMR, 13C NMR, and MS data. Thirteen compounds showed moderate to good anti-hyperglycaemic activity in glucose fed hyperglycaemic normal rats at the dose of 0.05 mM/kg b.w. On the basis of docking results nine compounds (2a, 2c, 2e, 2h, 2k, 2l, 2n, 2o and 2q) were evaluated for their ability to inhibit rat lens aldose reductase. Out of these six compounds (2h, 2k, 2l, 2n, 2o and 2q) were found more effective than the known ARI sorbinil. Five compounds (2h, 2k, 2l, 2n and 2o) showed significant dual action (anti-hyperglycaemic and aldose reductase inhibition).

Graphical abstractFive compounds (2h, 2k, 2l, 2n and 2o) showed significant dual action (anti-hyperglycaemic and ARI). Two compounds 2g and 2m showed anti-hyperglycaemic activity comparable to standard drug gliclazide.Figure optionsDownload full-size imageDownload as PowerPoint slide