Synthesis and Evaluation of Novel -alkyl Phthalimide- and -benzyl-oxadiazole-quinoline Hybrids as Inhibitors of Monoamine Oxidase and Acetylcholinesterase.

New -alkyl phthalimide - and -benzyl - analogs of 5-(2-phenylquinolin-4-yl)-1,3,4-oxadiazole-2-thiol () were prepared by reacting with -bromoalkylphthalimide and CF-substituted benzyl bromides in excellent yields. Spectroscopic techniques were employed to elucidate the structures of the synthesized molecules. The inhibition activity of newly synthesized molecules toward MAO-A, MAO-B, and AChE enzymes, was also assessed. All these compounds showed activity in the submicromolar range against all enzymes. Compounds and were found to be the most potent compounds against MAO-A (IC = 0.91 ± 0.15 nM) and MAO-B (IC = 0.84 ± 0.06 nM), while compound showed the most efficient acetylcholinesterase inhibition (IC = 1.02± 0.65 μM). Docking predictions disclosed the docking poses of the synthesized molecules with all enzymes and demonstrated the outstanding potency of compounds , , and (docking scores = -11.6, -15.3, and -14.0 kcal/mol against MAO-A, MAO-B, and AChE, respectively). These newly synthesized analogs act as up-and-coming candidates for the creation of safer curative use against Alzheimer's illness.