Discovery and Optimization of α-Mangostin Derivatives as Novel PDE4 Inhibitors for the Treatment of Vascular Dementia

J Med Chem. 2020 Mar 26;63(6):3370-3380. doi: 10.1021/acs.jmedchem.0c00060. Epub 2020 Mar 12.

Abstract

To validate PDE4 inhibitors as novel therapeutic agents against vascular dementia (VaD), 25 derivatives were discovered from the natural inhibitor α-mangostin (IC50 = 1.31 μM). Hit-to-lead optimization identified a novel and selective PDE4 inhibitor 4e (IC50 = 17 nM), which adopted a different binding pattern from PDE4 inhibitors roflumilast and rolipram. Oral administration of 4e at a dose of 10 mg/kg exhibited remarkable therapeutic effects in a VaD model and did not cause emesis to beagle dogs, indicating its potential as a novel anti-VaD agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopyridines / metabolism
  • Animals
  • Benzamides / metabolism
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / chemistry
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / metabolism
  • Cyclopropanes / metabolism
  • Dementia, Vascular / drug therapy*
  • Dogs
  • Drug Design
  • Humans
  • Male
  • Mice, Inbred C57BL
  • Molecular Structure
  • Phosphodiesterase 4 Inhibitors / chemical synthesis
  • Phosphodiesterase 4 Inhibitors / metabolism
  • Phosphodiesterase 4 Inhibitors / pharmacokinetics
  • Phosphodiesterase 4 Inhibitors / therapeutic use*
  • Protein Binding
  • Rolipram / metabolism
  • Rolipram / therapeutic use
  • Structure-Activity Relationship
  • Vomiting / prevention & control
  • Xanthones / chemical synthesis
  • Xanthones / metabolism
  • Xanthones / pharmacokinetics
  • Xanthones / therapeutic use*

Substances

  • Aminopyridines
  • Benzamides
  • Cyclopropanes
  • Phosphodiesterase 4 Inhibitors
  • Xanthones
  • Roflumilast
  • Cyclic Nucleotide Phosphodiesterases, Type 4
  • PDE4D protein, mouse
  • Rolipram
  • mangostin