7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one
[CAS# 73942-87-7]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one
• Synonyms: 1,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• CAS Registry Number: 73942-87-7
• EC Number: 616-033-4
• SMILES: COC1=C(C=C2C=CNC(=O)CC2=C1)OC

Properties

• Density: 1.167 mg/mL

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is a heterocyclic compound belonging to the class of benzazepines. These types of compounds have drawn significant attention in medicinal chemistry due to their diverse biological properties. The structure of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one consists of a benzene ring fused with a seven-membered azepine ring, with methoxy groups at the 7- and 8-positions and a lactam group at the 2-position of the azepine ring. The presence of these substituents makes this compound interesting for the development of novel therapeutic agents.

The discovery of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is rooted in the search for biologically active compounds that could serve as templates for the development of drugs targeting a variety of diseases. Benzazepines, in particular, have been studied for their potential in treating neurological disorders, such as Parkinson’s disease, as well as their antipsychotic and antidepressant properties. The addition of methoxy groups at specific positions on the aromatic ring enhances the compound's bioactivity, making it a promising candidate for pharmaceutical development.

The primary application of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one lies in its potential as a therapeutic agent for treating central nervous system (CNS) disorders. Compounds with benzazepine structures have been found to exhibit affinity for various receptors, including dopamine, serotonin, and adrenergic receptors, which are key targets in the treatment of conditions like Parkinson’s disease, schizophrenia, and depression. The presence of the methoxy groups in this compound is known to increase its solubility and receptor-binding affinity, thus enhancing its therapeutic potential. As such, 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one could serve as a lead compound for the development of novel CNS-active drugs.

Additionally, 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one has also been explored for its anti-inflammatory and antioxidant properties. Inflammation and oxidative stress are underlying factors in many chronic diseases, including neurodegenerative diseases, cardiovascular diseases, and cancer. The compound's ability to modulate inflammatory pathways and reduce oxidative damage makes it a potential candidate for the development of drugs aimed at managing such conditions. Its pharmacological profile can be further optimized through structural modifications to enhance potency and selectivity for specific therapeutic targets.

Furthermore, research has extended to the potential use of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one in the field of cancer treatment. The benzazepine scaffold has shown promise in binding to enzymes and receptors involved in cancer cell proliferation and survival. Modifications to the compound's structure, including the introduction of different substituents on the aromatic ring or the lactam moiety, could improve its anti-cancer activity, making it a valuable lead compound in the development of targeted cancer therapies.

References

2024. Groundbreaking Benzofused Hybrid Drug: Light-Responsive Reversible Absorption and Release in Hydrogel for Treating Kashin-Beck Disease. Russian Journal of General Chemistry, 94(9).
DOI: 10.1134/s1070363224090160

2006. Ivabradine. Pharmaceutical Substances
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0081