Polycyclic maleimide-based derivatives as first dual modulators of neuronal calcium channels and GSK-3β for Alzheimer's disease treatment

Eur J Med Chem. 2019 Feb 1:163:394-402. doi: 10.1016/j.ejmech.2018.12.003. Epub 2018 Dec 3.

Abstract

Current healthcare has significantly increased the average life expectancy, leading to a consequently greater incidence of age-related diseases, such as Alzheimer's disease. Following a multitarget approach, in this paper a series of polycyclic maleimide-based derivatives were designed and synthesized aimed at simultaneously modulate neuronal calcium channels and glycogen synthase kinase 3-beta (GSK-3β), validated targets to combat Alzheimer' disease. Different structural modifications were performed on the polycyclic scaffold in order to investigate the structure-activity relationships and compound 10 emerged as a promising non-toxic lead compound, endowed with calcium modulating brain-addressed properties and significant GSK-3β inhibitory activity. Moreover, the easily affordable polycyclic core appears as a new appealing privileged structure in medicinal chemistry.

Keywords: Alzheimer's disease; Ca(2+) channels; Dual inhibitors; GSK-3β; Maleimide-based polycyclic scaffold.

MeSH terms

  • Alzheimer Disease / drug therapy*
  • Calcium Channels, N-Type / drug effects*
  • Glycogen Synthase Kinase 3 beta / antagonists & inhibitors
  • Glycogen Synthase Kinase 3 beta / drug effects*
  • Humans
  • Maleimides / chemical synthesis
  • Maleimides / pharmacology*
  • Polycyclic Compounds / chemical synthesis
  • Structure-Activity Relationship

Substances

  • Calcium Channels, N-Type
  • Maleimides
  • Polycyclic Compounds
  • Glycogen Synthase Kinase 3 beta