Discovery of N-[4-(Quinolin-4-yloxy)phenyl]benzenesulfonamides as Novel AXL Kinase Inhibitors

J Med Chem. 2018 Jul 26;61(14):6277-6292. doi: 10.1021/acs.jmedchem.8b00672. Epub 2018 Jul 9.

Abstract

The overexpression of AXL kinase has been described in many types of cancer. Due to its role in proliferation, survival, migration, and resistance, AXL represents a promising target in the treatment of the disease. In this study we present a novel compound family that successfully targets the AXL kinase. Through optimization and detailed SAR studies we developed low nanomolar inhibitors, and after further biological characterization we identified a potent AXL kinase inhibitor with favorable pharmacokinetic profile. The antitumor activity was determined in xenograft models, and the lead compounds reduced the tumor size by 40% with no observed toxicity as well as lung metastasis formation by 66% when compared to vehicle control.

MeSH terms

  • Animals
  • Axl Receptor Tyrosine Kinase
  • Benzenesulfonamides
  • Caco-2 Cells
  • Drug Design*
  • Humans
  • Mice
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Receptor Protein-Tyrosine Kinases / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology*
  • Tissue Distribution

Substances

  • Protein Kinase Inhibitors
  • Proto-Oncogene Proteins
  • Sulfonamides
  • Receptor Protein-Tyrosine Kinases
  • Axl Receptor Tyrosine Kinase