365242-16-6

Basic information

• Product Name: (7S)-7-Amino-5,7-dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one
• Synonyms: (7S)-7-Amino-5,7-dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one;(S)-7-amino-5-methyl-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one;6H-Dibenz[b,d]azepin-6-one, 7-amino-5,7-dihydro-5-methyl-, (7S)-
• CAS NO: 365242-16-6
• Molecular Formula: C₁₅H₁₄N₂O
• Molecular Weight: 238.28446
• Product Categories: Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 365242-16-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 506.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 6.94±0.20(Predicted)
• CAS DataBase Reference: (7S)-7-Amino-5,7-dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (7S)-7-Amino-5,7-dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one(365242-16-6)
• EPA Substance Registry System: (7S)-7-Amino-5,7-dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one(365242-16-6)

Safety Data

• Hazardous Substances Data: 365242-16-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A major component of γ-secretase inhibitors

Upstream product

• 959977-20-9 C₂₃H₂₀N₂O₃ 
• 209984-30-5 N-methyl-5H-dibenzo[b,d]azepin-6(7H)-one 

Downstream Products

• 209984-33-8 (S)-5-(N-Boc-L-alaninyl)amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 1398547-80-2 (S)-2-((S)-2-(3,5-difluorophenyl)-2-(methoxymethoxy)acetamido)-N-((S)-5-methyl-6-oxo-6,7-dihydro-5Hdibenzo[b,d]azepin-7-yl)propanamide 

Relevant articles and documents

New flurbiprofen derivatives: Synthesis, membrane affinity and evaluation of in vitro effect on β-amyloid levels

Alzheimer′s disease (AD) is characterized by irreversible and progressive loss of memory and cognition and profound neuronal loss. Current therapeutic strategies for the treatment of AD have been directed to a variety of targets with the aim of reversing or preventing the disease but, unfortunately, the available treatments often produce no significant clinical benefits. During the last decades compounds that inhibit or modulate γ-secretase, reducing β amyloid (Aβ) levels, have been considered as potential therapeutics for AD. Among these the (R)-enantiomer of flurbiprofen (FLU) seems to be very promising, but it shows low brain penetration. In this study, in order to improve the properties of FLU against Alzheimer′s pathogenesis we synthesized some novel FLU lipophilic analogues. Lipophilicity of the new molecules has been characterized in terms of clogP, log KC18/W and log K IAM/W values. Permeability has been determined in both gastrointestinal PAMPA (PAMPA-GI) at different pH values and in brain blood barrier PAMPA (PAMPA-BBB) models. They were also tested for their ability to inhibit in vitro γ-secretase activity using rat CTXTNA2 astrocytes. Interestingly, the investigated molecules demonstrated to reduce Aβ 42 levels without affecting the amyloid precursor protein APP level in a clear concentrations-dependent manner.

A multigram chemical synthesis of the γ-secretase inhibitor LY411575 and its diastereoisomers

An improved chemical synthesis of N-2((2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoyl)-N1-((7S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-l-alaninamide (LY411,575, 9a), a known γ-secretase inhibitor, is described. The key synthetic steps, which