Synthesis and biological evaluation of novel 4,5-bisindolyl-1,2,4-triazol-3-ones as glycogen synthase kinase-3β inhibitors and neuroprotective agents

Pharmazie. 2017 Dec 1;72(12):707-713. doi: 10.1691/ph.2017.7722.

Abstract

A series of novel 4,5-bisindolyl-1,2,4-triazol-3-ones were designed, prepared and evaluated for their glycogen synthase kinase (GSK)-3β inhibitory activities. Compounds exhibited favorable inhibitory potency towards GSK-3β kinase at the molecular level and in cells indicated by significantly reducing GSK-3β substrate Tau phosphorylation at Ser396 in primary neurons showing the inhibition of cellular GSK-3β. In an in vitro model of neuronal injury, compounds 6b, 6d and 6f prevented glutamate-induced neuronal death which was closely associated with cerebral ischemic stroke. Preliminary structure-activity relationship was examined and showed that different substituents on the indole ring had significant influences on the GSK-3β inhibitory potency. These findings may provide new insights into the development of novel GSK-3β inhibitors as neuroprotective agents.

MeSH terms

  • Animals
  • Brain Ischemia / prevention & control
  • Computer Simulation
  • Glycogen Synthase Kinase 3 beta / antagonists & inhibitors*
  • In Vitro Techniques
  • Neurons / drug effects*
  • Neurons / pathology
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Stroke / prevention & control
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Neuroprotective Agents
  • Protein Kinase Inhibitors
  • Triazoles
  • Glycogen Synthase Kinase 3 beta