Syntheses, in vitro, and in silico studies of rhodanine-based schiff bases as potential α-amylase inhibitors and radicals (DPPH and ABTS) scavengers

A two-step reaction method was used to synthesize a series of rhodanine-based Schiff bases (2-33) that were characterized using spectroscopic techniques. All compounds were assessed for alpha-amylase inhibitory and radical scavenging (DPPH and ABTS) activities. In comparison to the standard acarbose (IC50 = 9.08 +/- 0.07 mu M), all compounds demonstrated good to moderate alpha-amylase inhibitory activity (IC50 = 10.91 +/- 0.08-61.89 +/- 0.102 mu M). Compounds also demonstrated significantly higher DPPH (IC50 = 10.33 +/- 0.02-96.65 +/- 0.03 mu M) and ABTS (IC50 = 12.01 +/- 0.12-97.47 +/- 0.13 mu M) radical scavenging activities than ascorbic acid (DPPH, IC50 = 15.08 +/- 0.03 mu M; ABTS, IC50 = 16.09 +/- 0.17 mu M). The limited structure-activity relationship (SAR) suggests that the position and nature of the substituted groups on the phenyl ring have a vital role in varying inhibitory potential. Among the series, compounds with an electron-withdrawing group at the para position showed the highest potency. Kinetic studies revealed that the compounds followed a competitive mode of inhibition. Molecular docking results are found to agree with experimental findings, showing that compounds reside in the active pocket due to the main rhodanine moiety. [GRAPHICS] .

Automated summary

A series of rhodanine-based Schiff bases were synthesized and evaluated for their inhibitory activities against alpha-amylase and radical scavenging. The position and nature of the substituted groups on the phenyl ring were found to play a crucial role in the inhibitory potential, with compounds containing an electron-withdrawing group at the para position showing the highest potency.