Discovery of novel allosteric mitogen-activated protein kinase kinase (MEK) 1,2 inhibitors possessing bidentate Ser212 interactions

J Med Chem. 2012 May 24;55(10):4594-604. doi: 10.1021/jm2017094. Epub 2012 May 3.

Abstract

Using structure-based design, two novel series of highly potent biaryl amine mitogen-activated protein kinase kinase (MEK) inhibitors have been discovered. These series contain an H-bond acceptor, in a shifted position compared with previously disclosed compounds, and an adjacent H-bond donor, resulting in a bidentate interaction with the Ser212 residue of MEK1. The most potent compound identified, 1 (G-894), is orally active in in vivo pharmacodynamic and tumor xenograft models.

MeSH terms

  • Allosteric Regulation
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacokinetics
  • Benzofurans / pharmacology
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / pharmacokinetics
  • Benzothiazoles / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Female
  • Hydrogen Bonding
  • Indazoles / chemical synthesis*
  • Indazoles / pharmacokinetics
  • Indazoles / pharmacology
  • MAP Kinase Kinase 1 / antagonists & inhibitors*
  • MAP Kinase Kinase 2 / antagonists & inhibitors*
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Neoplasm Transplantation
  • Rats
  • Serine / metabolism*
  • Structure-Activity Relationship
  • Transplantation, Heterologous

Substances

  • 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (2-hydroxyethoxy)amide
  • Antineoplastic Agents
  • Benzofurans
  • Benzothiazoles
  • Indazoles
  • Serine
  • MAP Kinase Kinase 1
  • MAP Kinase Kinase 2

Associated data

  • PDB/3V04
  • PDB/3VO1