Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine derivatives as novel selective Axl inhibitors

Bioorg Med Chem Lett. 2021 Sep 15:48:128247. doi: 10.1016/j.bmcl.2021.128247. Epub 2021 Jul 13.

Abstract

Axl and Mer are members of the TAM (Tyro3-Axl-Mer) family of receptor tyrosine kinases. Previously, we reported that enzyme-mediated inhibition of Mer by an Axl/Mer dual inhibitor led to retinal toxicity in mice, whereas selective Axl inhibition by compound 1 did not. On the other hand, compound 1 showed low membrane permeability. Here, we designed and synthesized a novel series of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine derivatives and evaluated their Axl and Mer inhibitory activities, leading to identification of ER-001259851-000 as a potent and selective Axl inhibitor with drug-likeness and a promising pharmacokinetic profile in mice.

Keywords: Axl; Cancer; Inhibitor; Mer; Small molecule; Structure-activity relationships.

MeSH terms

  • Animals
  • Axl Receptor Tyrosine Kinase
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Humans
  • Mice
  • Microsomes, Liver / chemistry
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Proto-Oncogene Proteins / metabolism
  • Pyridines / chemical synthesis
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Receptor Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Receptor Protein-Tyrosine Kinases / metabolism
  • Structure-Activity Relationship
  • c-Mer Tyrosine Kinase / antagonists & inhibitors*
  • c-Mer Tyrosine Kinase / metabolism

Substances

  • Protein Kinase Inhibitors
  • Proto-Oncogene Proteins
  • Pyridines
  • Pyrimidines
  • tetrahydropyrido(4,3-d)pyrimidine
  • MERTK protein, human
  • Receptor Protein-Tyrosine Kinases
  • c-Mer Tyrosine Kinase
  • Axl Receptor Tyrosine Kinase