Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer's disease

Bioorg Med Chem Lett. 2004 Nov 15;14(22):5521-5. doi: 10.1016/j.bmcl.2004.09.006.

Abstract

High-throughput screening with cyclin-dependent kinase 5 (cdk5)/p25 led to the discovery of N-(5-isopropyl-thiazol-2-yl)isobutyramide (1). This compound is an equipotent inhibitor of cdk5 and cyclin-dependent kinase 2 (cdk2)/cyclin E (IC(50)=ca. 320nM). Parallel and directed synthesis techniques were utilized to explore the SAR of this series. Up to 60-fold improvements in potency at cdk5 and 12-fold selectivity over cdk2 were achieved.

MeSH terms

  • Alzheimer Disease / drug therapy*
  • Amides / chemical synthesis
  • Amides / therapeutic use*
  • CDC2-CDC28 Kinases / antagonists & inhibitors
  • Cyclin-Dependent Kinase 2
  • Cyclin-Dependent Kinase 5
  • Cyclin-Dependent Kinases / antagonists & inhibitors*
  • Drug Evaluation, Preclinical
  • Molecular Structure
  • Nerve Tissue Proteins / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / therapeutic use*

Substances

  • Amides
  • N-(5-isopropyl-thiazol-2-yl)isobutyramide
  • Nerve Tissue Proteins
  • TPPP protein, human
  • Thiazoles
  • 2-aminothiazole
  • Cyclin-Dependent Kinase 5
  • CDC2-CDC28 Kinases
  • Cyclin-Dependent Kinase 2
  • Cyclin-Dependent Kinases