Identification and Optimization of 4-Anilinoquinolines as Inhibitors of Cyclin G Associated Kinase

ChemMedChem. 2018 Jan 8;13(1):48-66. doi: 10.1002/cmdc.201700663. Epub 2017 Nov 27.

Abstract

4-Anilinoquinolines were identified as potent and narrow-spectrum inhibitors of the cyclin G associated kinase (GAK), an important regulator of viral and bacterial entry into host cells. Optimization of the 4-anilino group and the 6,7-quinoline substituents produced GAK inhibitors with nanomolar activity, over 50 000-fold selectivity relative to other members of the numb-associated kinase (NAK) subfamily, and a compound (6,7-dimethoxy-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine; 49) with a narrow-spectrum kinome profile. These compounds may be useful tools to explore the therapeutic potential of GAK in prevention of a broad range of infectious and systemic diseases.

Keywords: anilinoquinolines; antibacterial agents; chemical probes; cyclin G associated kinase (GAK).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Aniline Compounds / metabolism
  • Aniline Compounds / pharmacology
  • Binding Sites
  • Catalytic Domain
  • Drug Design
  • Endocytosis / drug effects
  • Humans
  • Intracellular Signaling Peptides and Proteins / antagonists & inhibitors
  • Intracellular Signaling Peptides and Proteins / metabolism*
  • Kinetics
  • Molecular Docking Simulation
  • Protein Binding
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacology
  • Protein Serine-Threonine Kinases / antagonists & inhibitors
  • Protein Serine-Threonine Kinases / metabolism*
  • Quinazolines / chemistry*
  • Quinazolines / metabolism
  • Quinazolines / pharmacology
  • Structure-Activity Relationship
  • Viruses / pathogenicity

Substances

  • Aniline Compounds
  • Intracellular Signaling Peptides and Proteins
  • Protein Kinase Inhibitors
  • Quinazolines
  • anilinoquinazoline
  • GAK protein, human
  • Protein Serine-Threonine Kinases