381233-77-8

Basic information

• Product Name: 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one
• Synonyms: 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one
• CAS NO: 381233-77-8
• Molecular Weight: 351.202
• Mol File: 381233-77-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one(381233-77-8)
• EPA Substance Registry System: 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one(381233-77-8)

Safety Data

• Hazardous Substances Data: 381233-77-8(Hazardous Substances Data)

Upstream product

• 381233-75-6 5-bromo-3-iodo-1,2-dihydropyridin-2-one 
• 381233-96-1 2-amino-3-iodo-5-bromopyridine 
• 1072-97-5 5-bromo-2-pyridylamine 
• 381233-76-7 5-bromo-1-phenyl-3-iodo-1,2-dihydropyridin-2-one 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 

Downstream Products

• 380918-24-1 1-phenyl-5-(3-pyridyl)-3-(2-cyanophenyl)-1,2-dihydropyridin-2-one 
• 380918-25-2 C₂₃H₁₅N₃O 
• 381250-74-4 3-(2-cyanophenyl)-1-phenyl-5-(tri-n-butyl stannyl)-1,2-dihydropyridin-2-one 

Relevant articles and documents

Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (Perampanel): A novel, noncompetitive α-amino-3-hydroxy-5- methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist

Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5- pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.