Design, Synthesis, and Biological Evaluation of a New Series of Biphenyl/Bibenzyl Derivatives Functioning as Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase

Molecules. 2017 Jan 20;22(1):172. doi: 10.3390/molecules22010172.

Abstract

Alzheimer's disease (AD), the most common form of dementia in adults, is a progressive neurodegenerative disorder of the brain characterized by loss of memory and steady deterioration of cognition. Here, a series of symmetrical molecules containing biphenyl/bibenzyl scaffolds (12-36) were designed, synthesized, and evaluated for their ability to inhibit both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). A biological evaluation showed that most of these biphenyl derivatives were potent AChE and BuChE inhibitors. Among them, compound 15 displayed the greatest ability to inhibit BuChE (IC50 = 0.74 µM) and was also a good AChE inhibitor (IC50 = 1.18 µM). Compound 19 was not only a potent AChE inhibitor (IC50 = 0.096 µM), but also a mild BuChE inhibitor (IC50 =1.25 µM). Overall, these results suggested that compound 19 may be a promising agent in the treatment of AD.

Keywords: Alzheimer’s disease; acetylcholinesterase inhibitors; biphenyl/bibenzyl derivatives; butyrylcholinesterase inhibitors; molecular docking.

MeSH terms

  • Acetylcholinesterase / metabolism*
  • Alzheimer Disease / drug therapy*
  • Animals
  • Bibenzyls / chemical synthesis*
  • Bibenzyls / chemistry
  • Bibenzyls / pharmacology*
  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / pharmacology*
  • Butyrylcholinesterase / metabolism*
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Drug Design
  • Humans
  • Molecular Docking Simulation
  • Rats
  • Structure-Activity Relationship

Substances

  • Bibenzyls
  • Biphenyl Compounds
  • Cholinesterase Inhibitors
  • biphenyl
  • Acetylcholinesterase
  • Butyrylcholinesterase