1,4-Dihydroindeno[1,2-c]pyrazoles as potent checkpoint kinase 1 inhibitors: extended exploration on phenyl ring substitutions and preliminary ADME/PK studies

Bioorg Med Chem Lett. 2007 Jul 1;17(13):3618-23. doi: 10.1016/j.bmcl.2007.04.055. Epub 2007 Apr 25.

Abstract

A study on substitutions at the four open positions on the phenyl ring of the 1,4-dihydroindeno[1,2-c]pyrazoles as potent CHK-1 inhibitors is described. Bis-substitution at both the 6- and 7-positions led to inhibitors with IC(50) values below 0.3nM. The compound with the best overall activities (36) was able to potentiate the anti-proliferative effect of doxorubicin in HeLa cells by at least 47-fold. Physicochemical, metabolic, and pharmacokinetic properties of selected inhibitors are also disclosed.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics*
  • Caco-2 Cells
  • Checkpoint Kinase 1
  • Chemistry, Pharmaceutical / methods*
  • DNA Damage
  • Drug Design
  • Drug Screening Assays, Antitumor*
  • Flow Cytometry
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Microsomes, Liver / metabolism
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacokinetics*
  • Protein Kinases / chemistry*
  • Protein Kinases / metabolism
  • Rats

Substances

  • Antineoplastic Agents
  • Protein Kinase Inhibitors
  • Protein Kinases
  • CHEK1 protein, human
  • Checkpoint Kinase 1
  • Chek1 protein, mouse
  • Chek1 protein, rat