Taha_2023_J.Mol.Struct_1285_135530

With the goal of developing potential cholinesterase pharmaco-therapeutics, a new class of thirty analogs oxindole-based chalcone were synthesized by reacting nitro substituted oxindole with various substituted benzaldehyde in the presence of a base in ethanol under reflux conditions. All the synthesized analogs were characterized through different spectroscopic and spectrometric techniques such as 1H NMR, 13C NMR, HREI-MS and tested for their ability to inhibit acetylcholinesterase and butyrylcholinesterase that exhibited a variable degree of inhibitory potential with IC50 values ranging from 0.20+/-0.010 to 11.20+/-0.30microM for acetylcholinesterase and 0.30+/-0.010microM to 13.20+/-0.30microM for butyrylcholinesterase as compared to the standard drug donepezil (IC50 value 2.16+/-0.12 and 4.5+/-0.11microM respectively). Analog 22 is the most potent among the series having an IC50 value 0.10+/-0.010microM for acetylcholinesterase and 0.30+/-0.010microM for butyrylcholinesterase. Structure-activity relationship of this series has been established which is mainly based on the position and nature of the substituent on the phenyl ring. Molecular docking study was also carried out to discover the binding affinity of active derivatives with enzymes.