209984-30-5

Basic information

• Product Name: 6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-
• Synonyms: 6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-;5,7-Dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one;5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one 5,7-Dihydro-5-methyl-6H-dibenz[b,d]azepin-6-one;5-Methyl-5H-dibenzo[b,d]azepin-6(7H);5-methyl-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one;5-methyl-7H-benzo[d][1]benzazepin-6-one
• CAS NO: 209984-30-5
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.274
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 209984-30-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 155-160℃
• Boiling Point: 474.1 °C at 760 mmHg
• Flash Point: 238.5 °C
• Appearance: /
• Density: 1.166
• Vapor Pressure: 3.7E-09mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane, Methanol
• CAS DataBase Reference: 6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-(209984-30-5)
• EPA Substance Registry System: 6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-(209984-30-5)

Safety Data

• Hazardous Substances Data: 209984-30-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An intermediate in the production of γ-secretase inhibitors.

InChI:InChI=1/C15H13NO/c1-16-14-9-5-4-8-13(14)12-7-3-2-6-11(12)10-15(16)17/h2-9H,10H2,1H3

Upstream product

• 20011-90-9 5H,7H-dibenzo[b,d]azepin-6-one 
• 74-88-4 methyl iodide 
• 14925-09-8 2-(N-methylamino)-1,1'-biphenyl 
• 90-41-5 2-phenylaniline 
• 1243327-76-5 N-(2'-bromobiphenyl-2-yl)-N-methylacetamide 
• 955879-95-5 N-([1,1'-biphenyl]-2-yl)-2-chloro-N-methylacetamide 
• 683277-83-0 (2'-azido-biphenyl-2-yl)-acetic acid pentafluorophenyl ester 
• 325141-76-2 2-{2'-amino-[1,1'-biphenyl]-2-yl}acetonitrile 
• 615-36-1 2-bromoaniline 
• 40400-15-5 2-(2-iodophenyl)acetonitrile 
• 683277-82-9 (2'-azido-biphenyl-2-yl)-acetic acid 
• 683277-81-8 (2'-azido-biphenyl-2-yl)-acetonitrile 

Downstream Products

• 213024-76-1 7-amino-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride 
• 209994-99-0 7-(L-alaninyl)-amino-5-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 365242-16-6 (S)-5-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 733725-44-5 (R)-5-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 209984-31-6 7-methyl-5-oximo-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 

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.

Synthesis of dibenzazepinones by palladium-catalyzed intramolecular arylation of o -(2′-Bromophenyl)anilide enolates

A new approach for the convenient synthesis of dibenzazepinones is reported. The key step is the formation of the seven-membered ring through palladium-catalyzed intramolecular arylation of an anilide enolate. T'e reactions were completed in 10 min at 100 °C with moderate to excellent yields. Aminodibenzazepinone 1, the core structure in the γ-secretase inhibitor LY411575, can be prepared in five steps from 2-bromophenylboronic acid and 2-iodoaniline in 60% overall yield. The synthesis reported here compares favorably with presently available approaches to this interesting ring system.

CYCLOALKYL, LACTAM, LACTONE AND RELATED COMPOUNDS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND METHODS FOR INHIBITING BETA-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS BY USE OF SUCH COMPOUNDS

Disclosed are compounds which inhibit beta -amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits beta -amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.