Structure-Based Design of 6-Chloro-4-aminoquinazoline-2-carboxamide Derivatives as Potent and Selective p21-Activated Kinase 4 (PAK4) Inhibitors

J Med Chem. 2018 Jan 11;61(1):265-285. doi: 10.1021/acs.jmedchem.7b01342. Epub 2017 Dec 30.

Abstract

Herein, we report the discovery and characterization of a novel class of PAK4 inhibitors with a quinazoline scaffold. Based on the shape and chemical composition of the ATP-binding pocket of PAKs, we chose a 2,4-diaminoquinazoline series of inhibitors as a starting point. Guided by X-ray crystallography and a structure-based drug design (SBDD) approach, a series of novel 4-aminoquinazoline-2-carboxamide PAK4 inhibitors were designed and synthesized. The inhibitors' selectivity, therapeutic potency, and pharmaceutical properties were optimized. One of the best compounds, 31 (CZh226), showed remarkable PAK4 selectivity (346-fold vs PAK1) and favorable kinase selectivity profile. Moreover, this compound potently inhibited the migration and invasion of A549 tumor cells by regulating the PAK4-directed downstream signaling pathways in vitro. Taken together, these data support the further development of 31 as a lead compound for PAK4-targeted anticancer drug discovery and as a valuable research probe for the further biological investigation of group II PAKs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalytic Domain
  • Drug Design*
  • Humans
  • Models, Molecular
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacology*
  • Quinazolines / chemistry*
  • Quinazolines / metabolism
  • Quinazolines / pharmacology*
  • Structure-Activity Relationship
  • Substrate Specificity
  • p21-Activated Kinases / antagonists & inhibitors*
  • p21-Activated Kinases / chemistry
  • p21-Activated Kinases / metabolism

Substances

  • 4-aminoquinazoline
  • Protein Kinase Inhibitors
  • Quinazolines
  • PAK4 protein, human
  • p21-Activated Kinases