19301-09-8

Basic information

• Product Name: 1H-Benzo[d]azepin-2(3H)-one
• Synonyms: 1H-Benzo[d]azepin-2(3H)-one;2H-3-Benzazepin-2-one, 1,3-dihydro-;1,3-dihydro-2H-3-Benzazepin-2-one
• CAS NO: 19301-09-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• Mol File: 19301-09-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Benzo[d]azepin-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzo[d]azepin-2(3H)-one(19301-09-8)
• EPA Substance Registry System: 1H-Benzo[d]azepin-2(3H)-one(19301-09-8)

Safety Data

• Hazardous Substances Data: 19301-09-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzo[d]azepin-2(3H)-one is used as a reactant for the synthesis of 7-sulfonamido-3-benzazepines, which are potent and selective 5-HT2C receptor agonists. These agonists have potential applications in the treatment of various central nervous system disorders, such as schizophrenia, anxiety, and depression, due to their ability to modulate serotonin signaling in the brain.

Upstream product

• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 89314-87-4 Benzylpenilloaldehyd-dimethylacetal 

Downstream Products

• 15987-50-5 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one 
• 92460-21-4 3-(3-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-propyl)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 

Relevant articles and documents

7-Sulfonamido-3-benzazepines as potent and selective 5-HT2C receptor agonists: Hit-to-lead optimization

New 7-sulfonamido-3-benzazepines 3 are disclosed as 5-HT2C receptor agonists. Appropriate substitution of the amino group (R1R2N-) gave compounds that were potent 5-HT2C agonists with minimal activation of the 5-HT2A and 5-HT2B receptors. Furthermore, representative examples had excellent in vitro ADME properties and good selectivity over ion channel activity.

Specific bradycardic agents. 1. Chemistry, pharmacology, and structure-activity relationships of substituted benzazepinones, a new class of compounds exerting antiischemic properties

Structural modification of the calcium-antagonist verapamil (1) by replacement of the lipophilic α-isopropylacetonitrile moiety by various heterocyclic ring systems has led to a new class of cardiovascular compounds which are characterized by a specific bradycardic activity. These agents reduce heart rate without binding to classical calcium channels or β-adrenoceptors, interacting instead specifically with structures at the sino atrial node. Therefore they have also been termed sinus node inhibition. The prototype falipamil (2) has been submitted to furthr optimization mainly hy manipulation of the phthalimidine moiety. This has resultd in a secod generation of specific bradycardic agents with increased potency and selectively and prolonged duration of action represented by the benzazepinone-derivative UL-FS 49 (4). Structure-activity relationships within this novel class of compounds have revealed a marked dependence of activity on the substitution pattern of the aromatic rings, the nature of the central nitrogen atom, and the length of the connecting alkyl chains. The crucial role of the benzazepione ring for bradycardic activity can be best explained by its special impact on the overall molecular conformation.