Imidazo[1,5-a][1,2,4]-triazolo[1,5-d][1,4]benzodiazepines as potent and highly selective GABAA alpha5 inverse agonists with potential for the treatment of cognitive dysfunction

Bioorg Med Chem Lett. 2009 Oct 15;19(20):5958-61. doi: 10.1016/j.bmcl.2009.08.027. Epub 2009 Aug 11.

Abstract

In a search for GABAA alpha5 ligands that combine high subtype binding selectivity with a marked inverse agonism imidazo[1,5-a][1,2,4]-triazolo[1,5-d][1,4]benzodiazepines were identified as a promising class. A short tandem reaction allowed rapid access to this chemical series, thereby facilitating rapid SAR generation which guided the optimization process. Two compounds (10e and 11f) were found to be active in an in vivo paradigm for cognitive improvement.

MeSH terms

  • Adjuvants, Anesthesia / pharmacology
  • Animals
  • Anticonvulsants / chemical synthesis
  • Anticonvulsants / chemistry*
  • Anticonvulsants / pharmacokinetics
  • Benzodiazepines / chemical synthesis
  • Benzodiazepines / chemistry*
  • Benzodiazepines / pharmacokinetics
  • Benzodiazepines / pharmacology
  • Cell Line
  • Cognition Disorders / drug therapy*
  • Drug Inverse Agonism
  • GABA-A Receptor Agonists
  • Humans
  • Memory, Short-Term / drug effects
  • Microsomes, Liver / metabolism
  • Rats
  • Receptors, GABA-A / metabolism*
  • Scopolamine / pharmacology
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology

Substances

  • Adjuvants, Anesthesia
  • Anticonvulsants
  • GABA-A Receptor Agonists
  • Receptors, GABA-A
  • Triazoles
  • Benzodiazepines
  • Scopolamine