3-Amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: a new class of CDK2 inhibitors

Bioorg Med Chem Lett. 2006 Feb 15;16(4):1084-90. doi: 10.1016/j.bmcl.2005.10.071. Epub 2005 Nov 14.

Abstract

We have recently reported about a new class of Aurora-A inhibitors based on a bicyclic tetrahydropyrrolo[3,4-c]pyrazole scaffold. Here we describe the synthesis and early expansion of CDK2/cyclin A-E inhibitors belonging to the same chemical class. Synthesis of the compounds was accomplished using a solution-phase protocol amenable to rapid parallel expansion. Compounds with nanomolar activity in the biochemical assay and able to efficiently inhibit CDK2-mediated tumor cell proliferation have been obtained.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / classification
  • Antineoplastic Agents / pharmacology*
  • Aurora Kinases
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Cyclin A / antagonists & inhibitors
  • Cyclin-Dependent Kinase 2 / antagonists & inhibitors*
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / classification
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Protein Serine-Threonine Kinases / antagonists & inhibitors
  • Pyrazoles / chemical synthesis
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Cyclin A
  • Enzyme Inhibitors
  • Pyrazoles
  • Aurora Kinases
  • Protein Serine-Threonine Kinases
  • CDK2 protein, human
  • Cyclin-Dependent Kinase 2