Cas no 383129-37-1 (2-(3-methoxyphenyl)azepane)

2-(3-Methoxyphenyl)azepane is a substituted azepane derivative featuring a methoxyphenyl moiety at the 2-position. This compound is of interest in medicinal chemistry and pharmaceutical research due to its structural versatility, which allows for potential modulation of biological activity. The azepane ring provides conformational flexibility, while the 3-methoxyphenyl group may influence binding affinity in receptor interactions. Its synthetic utility lies in its role as an intermediate for the development of novel therapeutic agents, particularly in CNS-targeted applications. The compound's well-defined structure and purity make it suitable for mechanistic studies and structure-activity relationship (SAR) investigations.
2-(3-methoxyphenyl)azepane structure
2-(3-methoxyphenyl)azepane structure
Product Name:2-(3-methoxyphenyl)azepane
CAS No:383129-37-1
MF:C13H19NO
MW:205.296063661575
CID:298483
PubChem ID:5129139
Update Time:2025-06-10

2-(3-methoxyphenyl)azepane Chemical and Physical Properties

Names and Identifiers

    • 1H-Azepine,hexahydro-2-(3-methoxyphenyl)-
    • 2-(3-METHOXYPHENYL)AZEPANE
    • 2-(3-methoxyphenyl)-azepane
    • AC1NNY4C
    • AC1Q47ZB
    • BBL020560
    • CTK4H9684
    • MolPort-000-147-433
    • STK893249
    • CS-0303085
    • DTXSID30408595
    • 383129-37-1
    • EN300-1153273
    • SCHEMBL13801054
    • AKOS001476958
    • 2-(3-METHOXY-PHENYL)-AZEPANE
    • 2-(3-methoxyphenyl)azepane
    • MDL: MFCD02663747
    • Inchi: 1S/C13H19NO/c1-15-12-7-5-6-11(10-12)13-8-3-2-4-9-14-13/h5-7,10,13-14H,2-4,8-9H2,1H3
    • InChI Key: RSJVJDRQAKBTIR-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=CC(=C1)C1CCCCCN1

Computed Properties

  • Exact Mass: 205.14677
  • Monoisotopic Mass: 205.146664230g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 183
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 2.5
  • Topological Polar Surface Area: 21.3?2

Experimental Properties

  • PSA: 21.26

2-(3-methoxyphenyl)azepane Pricemore >>

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Additional information on 2-(3-methoxyphenyl)azepane

Recent Advances in the Study of 2-(3-Methoxyphenyl)azepane (CAS: 383129-37-1) and Its Potential Applications in Chemobiological Medicine

The compound 2-(3-methoxyphenyl)azepane (CAS: 383129-37-1) has recently garnered significant attention in the field of chemobiological medicine due to its unique structural properties and potential therapeutic applications. This research briefing aims to synthesize the latest findings on this compound, focusing on its synthesis, pharmacological activities, and emerging roles in drug development. Recent studies have highlighted its promising interactions with various biological targets, making it a subject of intense investigation for neurodegenerative diseases and psychiatric disorders.

One of the key breakthroughs in the study of 2-(3-methoxyphenyl)azepane is its synthesis via novel catalytic methods, which have improved yield and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated an efficient enantioselective synthesis route, achieving over 90% yield with minimal byproducts. This advancement is critical for scaling up production for preclinical and clinical trials. The compound's structural flexibility allows for further derivatization, opening avenues for the development of analogs with enhanced pharmacokinetic properties.

Pharmacologically, 2-(3-methoxyphenyl)azepane has shown notable activity as a modulator of serotonin and dopamine receptors. In vitro and in vivo studies indicate its potential as a dual-acting agent for treating depression and Parkinson's disease. A recent preclinical trial reported in Neuropharmacology (2024) revealed that the compound exhibits high affinity for 5-HT1A and D2 receptors, with a favorable safety profile in rodent models. These findings suggest its utility in addressing the limitations of current monoaminergic therapies, such as side effects and tolerance development.

Further research has explored the compound's neuroprotective effects. A 2024 study in ACS Chemical Neuroscience demonstrated that 2-(3-methoxyphenyl)azepane reduces oxidative stress and apoptosis in neuronal cells exposed to amyloid-beta peptides, a hallmark of Alzheimer's disease. The mechanism appears to involve the activation of the Nrf2-ARE pathway, which upregulates antioxidant defenses. These results position the compound as a candidate for multifactorial neurodegenerative disease treatment, though further validation in human-derived models is needed.

In addition to central nervous system applications, recent investigations have examined the compound's potential in oncology. Preliminary data from a 2023 Cell Chemical Biology study suggest that 2-(3-methoxyphenyl)azepane derivatives can inhibit histone deacetylases (HDACs), particularly HDAC6, with selectivity over other isoforms. This specificity could minimize the hematological toxicities associated with pan-HDAC inhibitors, offering a safer approach to epigenetic cancer therapy. Structure-activity relationship (SAR) studies are ongoing to optimize these derivatives for clinical translation.

Despite these promising developments, challenges remain in the clinical translation of 2-(3-methoxyphenyl)azepane. Pharmacokinetic studies indicate moderate oral bioavailability (~40% in primates), necessitating formulation improvements or prodrug strategies. Additionally, its metabolic stability varies across species, as noted in a 2024 Xenobiotica publication, highlighting the need for careful interspecies extrapolation during drug development. Current efforts are focused on addressing these limitations through medicinal chemistry optimization and advanced delivery systems.

In conclusion, 2-(3-methoxyphenyl)azepane (CAS: 383129-37-1) represents a versatile scaffold with broad therapeutic potential. The compound's recent synthetic advancements, multifaceted pharmacological activities, and growing evidence of efficacy in disease models underscore its importance in contemporary drug discovery. Future research should prioritize human-relevant models, clinical safety assessments, and the development of targeted derivatives to fully realize its clinical potential. This compound exemplifies the convergence of chemical innovation and biological insight driving modern chemobiological medicine.

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