New indole derivatives as multitarget anti-Alzheimer's agents: synthesis, biological evaluation and molecular dynamics

Future Med Chem. 2023 Mar;15(6):473-495. doi: 10.4155/fmc-2022-0228. Epub 2023 Apr 26.

Abstract

Background: Alzheimer's disease is a neurological disorder that causes brain cells to shrink and die. Aim: Thirteen novel 'oxathiolanyl', 'pyrazolyl' and 'pyrimidinyl' indole derivatives were designed and synthesized as anti-Alzheimer's disease treatment. Method: In vitro enzyme assay was performed against both AChE and BChE enzymes. In addition, antioxidant assay and cytotoxicity on a normal cell line were determined. Molecular docking and dynamic simulations were conducted to confirm the binding mode in both esterases' active sites. In silico absorption, distribution, metabolism, excretion and toxicity studies were also carried out. Results & conclusion: Compounds 5, 7 and 11 exhibited superior inhibitory activity against acetylcholinesterase and butyrylcholinesterase, with IC50 values of 0.042 and 3.003 μM, 2.54 and 0.207 μM and 0.052 and 2.529 μM, respectively, compared with donepezil.

Keywords: AChE; Alzheimer's disease; BChE; indole derivatives; molecular dynamic simulations.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alzheimer Disease* / drug therapy
  • Butyrylcholinesterase* / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Cholinesterase Inhibitors / therapeutic use
  • Humans
  • Indoles / pharmacology
  • Molecular Docking Simulation
  • Molecular Dynamics Simulation
  • Structure-Activity Relationship

Substances

  • Butyrylcholinesterase
  • Acetylcholinesterase
  • Cholinesterase Inhibitors
  • Indoles