Design, synthesis and evaluation of vilazodone-tacrine hybrids as multitarget-directed ligands against depression with cognitive impairment

Bioorg Med Chem. 2018 Jul 23;26(12):3117-3125. doi: 10.1016/j.bmc.2018.04.037. Epub 2018 Apr 18.

Abstract

Depression, a severe mental disease, is greatly difficult to treat and easy to induce other neuropsychiatric symptoms, the most frequent one is cognitive impairment. In this study, a series of novel vilazodone-tacrine hybrids were designed, synthesized and evaluated as multitarget agents against depression with cognitive impairment. Most compounds exhibited good multitarget activities and appropriate blood-brain barrier permeability. Specifically, compounds 1d and 2a exhibited excellent 5-HT1A agonist activities (1d, EC50 = 0.36 ± 0.08 nM; 2a, EC50 = 0.58 ± 0.14 nM) and 5-HT reuptake inhibitory activities (1d, IC50 = 20.42 ± 6.60 nM; 2a, IC50 = 22.10 ± 5.80 nM). In addition, they showed moderate ChE inhibitory activities (1d, AChE IC50 = 1.72 ± 0.217 μM, BuChE IC50 = 0.34 ± 0.03 μM; 2a, AChE IC50 = 2.36 ± 0.34 μM, BuChE IC50 = 0.10 ± 0.01 μM). Good multitarget activities with goodt blood-brain barrier permeability of 1d and 2a make them good lead compounds for the further study of depression with cognitive impairment.

Keywords: 5-HT reuptake inhibition; 5-HT(1A) agonist; ChE inhibition; Cognitive impairment; Depression; Multitarget-directed ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / complications
  • Alzheimer Disease / drug therapy
  • Alzheimer Disease / pathology
  • Animals
  • Blood-Brain Barrier / metabolism
  • Butyrylcholinesterase / chemistry
  • Butyrylcholinesterase / metabolism
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / pharmacology
  • Cholinesterase Inhibitors / therapeutic use
  • Depression / complications
  • Depression / drug therapy
  • Depression / pathology
  • Drug Design*
  • Ligands*
  • Mice
  • Permeability / drug effects
  • Serotonin 5-HT1 Receptor Agonists / chemical synthesis*
  • Serotonin 5-HT1 Receptor Agonists / pharmacology
  • Serotonin 5-HT1 Receptor Agonists / therapeutic use
  • Structure-Activity Relationship
  • Tacrine / chemistry*
  • Vilazodone Hydrochloride / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Ligands
  • Serotonin 5-HT1 Receptor Agonists
  • Tacrine
  • Acetylcholinesterase
  • Butyrylcholinesterase
  • Vilazodone Hydrochloride