An Efficient Ionic Liquid Mediated Synthesis, Cholinesterase Inhibitory Activity and Molecular Modeling Study of Novel Piperidone Embedded α ,β-Unsaturated Ketones
Raju Suresh Kumar,
Kooi Yeong Khaw,
Mohd. Mustaqim Rosli.
A series of hitherto unreported piperidone embedded α,β-unsaturated ketones were synthesized efficiently in
ionic solvent and evaluated for cholinesterase inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase
(BChE) enzymes. Most of the synthesized compounds displayed good enzyme inhibition; therein compounds
7i and 7f displayed significant activity against AChE with IC50 values of 1.47 and 1.74 µM, respectively. Compound 6g
showed the highest BChE inhibitory potency with IC50 value of 3.41 µM, being 5 times more potent than galanthamine.
Molecular modeling simulation was performed using AChE and BChE receptors extracted from crystal structure of human
AChE and human BChE to determine the amino acid residues involved in the binding interaction of synthesized
compounds and their relevant receptors.
Keywords: AChE, BChE, Claisen-Schmidt Condensation, Chalcones, Molecular modeling.
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