An efficient ionic liquid mediated synthesis, cholinesterase inhibitory activity and molecular modeling study of novel piperidone embedded α,β-unsaturated ketones

Yalda Kia, Hasnah Osman, Raju Suresh Kumar, Vikneswaran Murugaiyah, Alireza Basiri, Kooi Yeong Khaw, Mohd Mustaqim Rosli

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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.

Original languageEnglish
Pages (from-to)512-520
Number of pages9
JournalMedicinal Chemistry
Issue number5
Publication statusPublished - Aug 2014
Externally publishedYes


  • AChE
  • BChE
  • Chalcones
  • Claisen-Schmidt Condensation
  • Molecular modeling

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