Discovery of pyrroloaminopyrazoles as novel PAK inhibitors

J Med Chem. 2012 May 24;55(10):4728-39. doi: 10.1021/jm300204j. Epub 2012 May 14.

Abstract

The P21-activated kinases (PAK) are emerging antitumor therapeutic targets. In this paper, we describe the discovery of potent PAK inhibitors guided by structure-based drug design. In addition, the efflux of the pyrrolopyrazole series was effectively reduced by applying multiple medicinal chemistry strategies, leading to a series of PAK inhibitors that are orally active in inhibiting tumor growth in vivo.

MeSH terms

  • Administration, Oral
  • Amides / chemical synthesis
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Carbamates / chemistry
  • Carbamates / pharmacokinetics
  • Carbamates / pharmacology
  • Crystallography, X-Ray
  • Dogs
  • Humans
  • Hydrogen Bonding
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Permeability
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacokinetics
  • Pyrazoles / pharmacology
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacokinetics
  • Pyrroles / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Burden / drug effects
  • Xenograft Model Antitumor Assays
  • p21-Activated Kinases / antagonists & inhibitors*

Substances

  • Amides
  • Antineoplastic Agents
  • Carbamates
  • Pyrazoles
  • Pyrroles
  • p21-Activated Kinases