Structure-activity relationships of 3,4-dihydro-1H-quinazolin-2-one derivatives as potential CDK5 inhibitors

Bioorg Med Chem. 2007 Oct 15;15(20):6574-95. doi: 10.1016/j.bmc.2007.07.005. Epub 2007 Jul 25.

Abstract

Cyclin-dependent kinase 5 (CDK5) is a serine/threonine kinase that plays a critical role in the early development of the nervous system. Deregulation of CDK5 is believed to contribute to the abnormal phosphorylation of various cellular substrates associated with neurodegenerative disorders such as Alzheimer's disease, amyotrophic lateral sclerosis, and ischemic stroke. Acyclic urea 3 was identified as a potent CDK5 inhibitor and co-crystallographic data of urea 3/CDK2 enzyme were used to design a novel series of 3,4-dihydroquinazolin-2(1H)-ones as CDK5 inhibitors. In this investigation we present our synthetic studies toward this series of compounds and discuss their biological relevance as CDK5 inhibitors.

MeSH terms

  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology
  • Benzyl Compounds / chemical synthesis
  • Benzyl Compounds / chemistry
  • Benzylamines / chemical synthesis
  • Benzylamines / chemistry
  • Binding Sites
  • Crystallography, X-Ray
  • Cyclin-Dependent Kinase 5 / antagonists & inhibitors*
  • Cyclin-Dependent Kinase 5 / metabolism
  • Hydrogen / chemistry
  • Inhibitory Concentration 50
  • Isomerism
  • Models, Molecular
  • Molecular Structure
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Quinazolinones / chemical synthesis
  • Quinazolinones / chemistry*
  • Quinazolinones / pharmacology*
  • Structure-Activity Relationship
  • Thiadiazoles / chemical synthesis
  • Thiadiazoles / chemistry
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry

Substances

  • Benzimidazoles
  • Benzyl Compounds
  • Benzylamines
  • Oxadiazoles
  • Protein Kinase Inhibitors
  • Quinazolinones
  • Thiadiazoles
  • Thiazoles
  • Hydrogen
  • benzylamine
  • benzimidazole
  • Cyclin-Dependent Kinase 5
  • benzyl bromide