1193004-31-7

Basic information

• Product Name: N₂-{7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}serinamide
• Synonyms: N₂-{7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}serinamide
• CAS NO: 1193004-31-7
• Molecular Weight: 388.807
• Mol File: 1193004-31-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N₂-{7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}serinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N₂-{7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}serinamide(1193004-31-7)
• EPA Substance Registry System: N₂-{7-[(3-chlorobenzyl)oxy]-2-oxo-2H-chromen-4-yl}serinamide(1193004-31-7)

Safety Data

• Hazardous Substances Data: 1193004-31-7(Hazardous Substances Data)

Upstream product

• 1193004-14-6 4-chloro-7-[(3-chlorobenzyl)oxy]-2H-chromen-2-one 
• 65414-74-6 L-serinamide hydrochloride 

Relevant articles and documents

Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: Development and biopharmacological profiling of 7-[(3-chlorobenzyl) oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor

In an effort to discover novel selective monoamine oxidase (MAO) B inhibitors with favorable physicochemical and pharmacokinetic profiles, 7-[(m-halogeno)benzyloxy]coumarins bearing properly selected polar substituents at position 4 were designed, synthesized, and evaluated as MAO inhibitors. Several compounds with MAO-B inhibitory activity in the nanomolar range and excellent MAO-B selectivity (selectivity index SI > 400) were identified. Structure-affinity relationships and docking simulations provided valuable insights into the enzyme-inhibitor binding interactions at position 4, which has been poorly explored. Furthermore, computational and experimental studies led to the identification and biopharmacological characterization of 7-[(3-chlorobenzyl)oxy]-4-[(methylamino)-methyl]-2H-chromen-2-one methanesulfonate 22b (NW-1772) as an in vitro and in vivo potent and selective MAO-B inhibitor, with rapid blood-brain barrier penetration, short-acting and reversible inhibitory activity, slight inhibition of selected cytochrome P450s, and low in vitro toxicity. On the basis of this preliminary preclinical profile, inhibitor 22b might be viewed as a promising clinical candidate for the treatment of neurodegenerative diseases.