Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors

Bioorg Med Chem. 2013 Mar 1;21(5):1064-73. doi: 10.1016/j.bmc.2013.01.015. Epub 2013 Jan 16.


A series of aloe-emodin derivatives were designed, synthesized and evaluated as acetylcholinesterase inhibitors. Most of the new prepared compounds showed remarkable acetylcholinesterase inhibitory activities. Among them, the compound 1-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl) methyl) pyridin-1-ium chloride (C3) which has a pyridinium substituent possessed the best inhibitory activity of acetylcholinesterase (IC(50)=0.09 μM). The docking study performed with AUTODOCK demonstrated that C3 could interact with the catalytic active site (CAS) and the peripheral anionic site (PAS) of acetylcholinesterase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry*
  • Acetylcholinesterase / metabolism
  • Anthraquinones / chemical synthesis
  • Anthraquinones / chemistry*
  • Anthraquinones / metabolism
  • Binding Sites
  • Catalytic Domain
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / metabolism
  • Drug Evaluation, Preclinical
  • Kinetics
  • Molecular Docking Simulation
  • Protein Binding
  • Structure-Activity Relationship
  • Tacrine / chemistry
  • Tacrine / metabolism


  • Anthraquinones
  • Cholinesterase Inhibitors
  • Tacrine
  • aloe emodin
  • Acetylcholinesterase