Synthesis and cholinesterase inhibitory activity study of new piperidone grafted spiropyrrolidines

Bioorg Chem. 2017 Dec:75:210-216. doi: 10.1016/j.bioorg.2017.09.019. Epub 2017 Sep 29.

Abstract

Alzheimer's disease (AD) is a prevalent neurodegenerative disorder, which affected 35 million people in the world. The most practiced approach to improve the life expectancy of AD patients is to increase acetylcholine neurotransmitter level at cholinergic synapses by inhibition of cholinesterase enzymes. A series of unreported piperidone grafted spiropyrrolidines 8(a-p) were synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Therein, compounds 8h and 8l displayed more potent AChE enzyme inhibition than standard drug with IC50 values of 1.88 and 1.37 µM, respectively. Molecular docking simulations for 8l possessing the most potent AChE inhibitory activities, disclosed its interesting binding templates to the active site channel of AChE enzymes. These compounds are remarkable AChE inhibitors and have potential as AD drugs.

Keywords: AChE and BChE activities; Ionic liquid; Molecular docking; Spiropyrrolidines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry*
  • Acetylcholinesterase / metabolism
  • Binding Sites
  • Butyrylcholinesterase / chemistry*
  • Butyrylcholinesterase / metabolism
  • Catalytic Domain
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / metabolism
  • Cholinesterase Inhibitors / pharmacology
  • Enzyme Activation / drug effects
  • Inhibitory Concentration 50
  • Ionic Liquids / chemistry
  • Molecular Docking Simulation
  • Piperidones / chemistry*
  • Piperidones / pharmacology
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry*
  • Pyrrolidines / metabolism
  • Pyrrolidines / pharmacology

Substances

  • Cholinesterase Inhibitors
  • Ionic Liquids
  • Piperidones
  • Pyrrolidines
  • Acetylcholinesterase
  • Butyrylcholinesterase