Phenylglycine and phenylalanine derivatives as potent and selective HDAC1 inhibitors (SHI-1)

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1859-63. doi: 10.1016/j.bmcl.2008.02.012. Epub 2008 Feb 10.

Abstract

An HTS screening campaign identified a series of low molecular weight phenols that showed excellent selectivity (>100-fold) for HDAC1/HDAC2 over other Class I and Class II HDACs. Evolution and optimization of this HTS hit series provided HDAC1-selective (SHI-1) compounds with excellent anti-proliferative activity and improved physical properties. Dose-dependent efficacy in a mouse HCT116 xenograft model was demonstrated with a phenylglycine SHI-1 analog.

MeSH terms

  • Acetylation
  • Amides
  • Animals
  • Cell Proliferation / drug effects*
  • Colonic Neoplasms / drug therapy*
  • Colonic Neoplasms / enzymology
  • Colonic Neoplasms / pathology
  • Dogs
  • ERG1 Potassium Channel
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Ether-A-Go-Go Potassium Channels / metabolism
  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Histone Deacetylase 1
  • Histone Deacetylase Inhibitors*
  • Humans
  • Macaca mulatta
  • Mice
  • Molecular Structure
  • Phenylalanine / chemistry*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • Xenograft Model Antitumor Assays

Substances

  • Amides
  • ERG1 Potassium Channel
  • Enzyme Inhibitors
  • Ether-A-Go-Go Potassium Channels
  • Histone Deacetylase Inhibitors
  • phenylglycine chloride
  • Phenylalanine
  • HDAC1 protein, human
  • Hdac1 protein, mouse
  • Histone Deacetylase 1
  • Glycine