N-(cycloalkylamino)acyl-2-aminothiazole inhibitors of cyclin-dependent kinase 2. N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4- piperidinecarboxamide (BMS-387032), a highly efficacious and selective antitumor agent

J Med Chem. 2004 Mar 25;47(7):1719-28. doi: 10.1021/jm0305568.

Abstract

N-Acyl-2-aminothiazoles with nonaromatic acyl side chains containing a basic amine were found to be potent, selective inhibitors of CDK2/cycE which exhibit antitumor activity in mice. In particular, compound 21 [N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide, BMS-387032], has been identified as an ATP-competitive and CDK2-selective inhibitor which has been selected to enter Phase 1 human clinical trials as an antitumor agent. In a cell-free enzyme assay, 21 showed a CDK2/cycE IC(50) = 48 nM and was 10- and 20-fold selective over CDK1/cycB and CDK4/cycD, respectively. It was also highly selective over a panel of 12 unrelated kinases. Antiproliferative activity was established in an A2780 cellular cytotoxicity assay in which 21 showed an IC(50) = 95 nM. Metabolism and pharmacokinetic studies showed that 21 exhibited a plasma half-life of 5-7 h in three species and moderately low protein binding in both mouse (69%) and human (63%) serum. Dosed orally to mouse, rat, and dog, 21 showed 100%, 31%, and 28% bioavailability, respectively. As an antitumor agent in mice, 21 administered at its maximum-tolerated dose exhibited a clearly superior efficacy profile when compared to flavopiridol in both an ip/ip P388 murine tumor model and in a s.c./i.p. A2780 human ovarian carcinoma xenograft model.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • CDC2-CDC28 Kinases / antagonists & inhibitors*
  • CDC2-CDC28 Kinases / metabolism
  • Cell Line, Tumor
  • Cell-Free System
  • Crystallography, X-Ray
  • Cyclin E / metabolism
  • Cyclin-Dependent Kinase 2
  • Dogs
  • Drug Screening Assays, Antitumor
  • Drug Stability
  • Humans
  • In Vitro Techniques
  • Mice
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Molecular Structure
  • Neoplasm Transplantation
  • Oxazoles / chemical synthesis*
  • Oxazoles / pharmacokinetics
  • Oxazoles / pharmacology
  • Phosphorylation
  • Rats
  • Retinoblastoma Protein / metabolism
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology
  • Transplantation, Heterologous

Substances

  • Antineoplastic Agents
  • Cyclin E
  • N-(5-(((5-(1,1-dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide
  • Oxazoles
  • Retinoblastoma Protein
  • Thiazoles
  • CDC2-CDC28 Kinases
  • CDK2 protein, human
  • Cdk2 protein, mouse
  • Cdk2 protein, rat
  • Cyclin-Dependent Kinase 2