Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2

J Med Chem. 2020 Jan 23;63(2):621-637. doi: 10.1021/acs.jmedchem.9b01582. Epub 2020 Jan 7.

Abstract

Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Discovery
  • Eukaryotic Initiation Factor-4E / antagonists & inhibitors
  • Humans
  • Intracellular Signaling Peptides and Proteins / antagonists & inhibitors*
  • Models, Molecular
  • Phosphorylation
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • EIF4E protein, human
  • Eukaryotic Initiation Factor-4E
  • Intracellular Signaling Peptides and Proteins
  • Protein Kinase Inhibitors
  • MKNK1 protein, human
  • MKNK2 protein, human
  • Protein Serine-Threonine Kinases