Cell Penetrant Inhibitors of the KDM4 and KDM5 Families of Histone Lysine Demethylases. 2. Pyrido[3,4-d]pyrimidin-4(3H)-one Derivatives

J Med Chem. 2016 Feb 25;59(4):1370-87. doi: 10.1021/acs.jmedchem.5b01538. Epub 2016 Jan 15.

Abstract

Following the discovery of cell penetrant pyridine-4-carboxylate inhibitors of the KDM4 (JMJD2) and KDM5 (JARID1) families of histone lysine demethylases (e.g., 1), further optimization led to the identification of non-carboxylate inhibitors derived from pyrido[3,4-d]pyrimidin-4(3H)-one. A number of exemplars such as compound 41 possess interesting activity profiles in KDM4C and KDM5C biochemical and target-specific, cellular mechanistic assays.

MeSH terms

  • Cell Line
  • Cell Membrane Permeability
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Histone Demethylases / antagonists & inhibitors*
  • Histone Demethylases / chemistry
  • Histone Demethylases / metabolism
  • Humans
  • Jumonji Domain-Containing Histone Demethylases / antagonists & inhibitors*
  • Jumonji Domain-Containing Histone Demethylases / chemistry
  • Jumonji Domain-Containing Histone Demethylases / metabolism
  • Models, Molecular
  • Molecular Docking Simulation
  • Pyrimidinones / chemistry*
  • Pyrimidinones / pharmacokinetics
  • Pyrimidinones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • KDM4C protein, human
  • Pyrimidinones
  • Histone Demethylases
  • Jumonji Domain-Containing Histone Demethylases
  • KDM4D protein, human
  • KDM5C protein, human