Synthesis, antidiabetic activity and molecular docking studies of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles.

Abstract

A series of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles synthesized in a straightforward route consisting of benzylidenethiazolidine-2,4-dione and 1,2,3-triazole pharmacophores. The new scaffolds tested for in vitro antidiabetic activity by inhibition of aldose reductase enzyme and its inhibition measured in half of Inhibition Concentration (IC50). The activity results correlated with standard reference Sorbinil (IC50: 3.45 ± 0.25µM). Among all the titled compounds 8f (1.42 ± 0.21µM), 8d (1.85 ± 0.39µM), 13a (1.94 ± 0.27µM) and 8b (1.98 ± 0.58µM) shown potent activity. In addition, molecular docking results against the crystal structure of aldose reductase (PDB ID: 1PWM) revealed that the binding affinities shown by all synthesized compounds are higher than the reference compound Sorbinil. The docking scores, H-bond interactions, and hydrophobic interactions well defined inhibition strength of all compounds.