Acetylphenyl-Substituted Imidazolium Salts: Synthesis, Characterization, in silico Studies and Inhibitory Properties against Some Metabolic Enzymes

Abstract

AbstractHerein, we present how to thirteen new synthesize 1-(4-acetylphenyl)-3-alkylimidazolium salts by reacting 4-(1-H-imidazol-1-yl)acetophenone with a variety of benzyl halides that contain either electron-donating or electron-withdrawing groups. The structures of the new imidazolium salts were conformed using different spectroscopic method (1H NMR,13C NMR,19F NMR and FTIR) and elemental analysis techniques. Furthermore, the carbonic anhydrase and acetylcholinesterase enzyme inhibition activities of these compounds were investigated. They showed highly potent inhibition effect toward acetylcholinesterase (AChE) and carbonic anhydrases (hCAs) with Kivalues in the range of 8.30±1.71 to 120.77±8.61 nM for AChE, 16.97±2.04 to 84.45±13.78 nM for hCA I, and 14.09±2.99 to 69.33±17.35 nM for hCA II, respectively. Most of the synthesized imidazolium salts were appeared to be more potent than the standard inhibitor of tacrine (TAC) against AChE, and Acetazolamide (AZA) against CA. In the meantime, to prospect for potential synthesized imidazolium salt inhibitor(s) against acetylcholinesterase (AChE) and carbonic anhydrases (hCAs), molecular docking and ADMET-based approach was exerted.