Schiff Base Synthesis with a New Reliable Method and Investigation of Their Inhibition Effects on Glutathione S-Transferase and Cholinesterase Enzymes

Abstract

The principle purpose of this study is to synthesize some Schiff base derivatives with a new microwave irradiation technique and investigate their enzyme inhibition effects. Related Schiff base compounds (1 a–1 h) were synthesized from 4-fluoro aniline and some substituted benzaldehyde derivatives (3 a–3 h). The chemical structures of Schiff bases were elucidated by various spectroscopic methods (1H NMR, 13C NMR). The inhibitory effects of the synthesized compounds against acetylcholinesterase, butyrylcholinesterase and glutathione S-transferase were investigated. The in vitro enzyme study determined the best enzyme inhibitors for AChE, BChE, and GST enzymes as 3 h, 3 b, and 3 e compounds, respectively. The results were compared with the standard drugs tacrine for cholinesterase and ethacrynic acid for GST enzymes. Molecular docking results demonstrated the low binding energy values between −5.8 kcal/mol and −8.7 kcal/mol with hydrogen bonding, hydrophilic, and hydrophobic interactions at the active catalytic sites of the enzymes. © 2023 Wiley-VCH GmbH.