Cas no 6933-50-2 (4-methoxy-9H-Carbazole)

4-Methoxy-9H-carbazole is a heterocyclic aromatic compound featuring a carbazole core substituted with a methoxy group at the 4-position. This structure imparts unique electronic and photophysical properties, making it valuable in organic synthesis and materials science. Its extended π-conjugation system enhances luminescence characteristics, rendering it suitable for applications in optoelectronic devices, such as OLEDs and organic semiconductors. The methoxy group further improves solubility in organic solvents, facilitating processing in thin-film fabrication. Additionally, 4-methoxy-9H-carbazole serves as a versatile intermediate in pharmaceutical research, particularly in the development of bioactive alkaloids. Its stability and functionalizability underscore its utility in advanced chemical and industrial applications.
4-methoxy-9H-Carbazole structure
4-methoxy-9H-Carbazole structure
Product Name:4-methoxy-9H-Carbazole
CAS No:6933-50-2
MF:C13H11NO
MW:197.232543230057
MDL:MFCD18452399
CID:1116161
PubChem ID:12655269
Update Time:2025-05-20

4-methoxy-9H-Carbazole Chemical and Physical Properties

Names and Identifiers

    • 4-methoxy-9H-Carbazole
    • 4-Methoxy-carbazol
    • 4-methoxycarbazole
    • 4-methoxy-carbazole
    • EN300-336041
    • LWPBIJIJIJTNOR-UHFFFAOYSA-N
    • SCHEMBL3362359
    • 6933-50-2
    • G69817
    • MDL: MFCD18452399
    • Inchi: 1S/C13H11NO/c1-15-12-8-4-7-11-13(12)9-5-2-3-6-10(9)14-11/h2-8,14H,1H3
    • InChI Key: LWPBIJIJIJTNOR-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=CC2=C1C1C=CC=CC=1N2

Computed Properties

  • Exact Mass: 197.08400
  • Monoisotopic Mass: 197.084063974g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 231
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.8
  • Topological Polar Surface Area: 25?2

Experimental Properties

  • PSA: 25.02000
  • LogP: 3.32970

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4-methoxy-9H-Carbazole Production Method

Additional information on 4-methoxy-9H-Carbazole

Recent Advances in the Study of 4-Methoxy-9H-Carbazole (CAS: 6933-50-2): A Promising Scaffold in Medicinal Chemistry

4-Methoxy-9H-carbazole (CAS: 6933-50-2) has emerged as a significant scaffold in medicinal chemistry due to its diverse pharmacological properties. Recent studies have highlighted its potential as a core structure for developing novel therapeutics, particularly in the fields of oncology, neurodegenerative diseases, and antimicrobial resistance. This research brief synthesizes the latest findings on the synthesis, biological activities, and mechanistic insights of 4-methoxy-9H-carbazole derivatives, providing a comprehensive overview for researchers in the chemical and biomedical fields.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of 4-methoxy-9H-carbazole derivatives in inhibiting protein kinases involved in cancer cell proliferation. The research team utilized structure-activity relationship (SAR) analysis to optimize the scaffold, resulting in compounds with nanomolar inhibitory concentrations against specific kinase targets. Molecular docking studies further elucidated the binding interactions, revealing key hydrogen bonds and hydrophobic interactions that contribute to the high affinity of these derivatives.

In the context of neurodegenerative diseases, a recent ACS Chemical Neuroscience publication (2024) reported that 4-methoxy-9H-carbazole analogs exhibit potent neuroprotective effects by modulating α-synuclein aggregation pathways. The study employed advanced biophysical techniques, including NMR spectroscopy and fluorescence anisotropy, to characterize the compound's interaction with amyloidogenic proteins. These findings suggest potential applications in Parkinson's disease therapeutics, with several derivatives showing blood-brain barrier permeability in in vivo models.

The antimicrobial potential of 4-methoxy-9H-carbazole derivatives has also gained attention, particularly in addressing multidrug-resistant bacterial strains. A 2024 study in European Journal of Medicinal Chemistry described novel carbazole-based compounds with broad-spectrum activity against Gram-positive pathogens, including MRSA. The researchers identified the methoxy group at position 4 as crucial for maintaining antibacterial activity while reducing cytotoxicity to mammalian cells, highlighting the importance of this structural feature in drug design.

From a synthetic chemistry perspective, recent advancements have focused on developing more efficient routes to 4-methoxy-9H-carbazole derivatives. A 2023 Organic Letters publication presented a novel palladium-catalyzed cyclization method that significantly improves yields and reduces reaction times compared to traditional approaches. This methodological breakthrough enables the rapid generation of diverse carbazole libraries for biological screening, accelerating drug discovery efforts.

The pharmacokinetic properties of 4-methoxy-9H-carbazole derivatives have been systematically investigated in several recent preclinical studies. Data from these studies indicate generally favorable absorption and metabolic stability profiles, though some derivatives show varying degrees of hepatic clearance. These findings underscore the need for continued optimization of the scaffold to enhance drug-like properties while maintaining biological activity.

Looking forward, the 4-methoxy-9H-carbazole scaffold presents numerous opportunities for further development. Current research directions include the exploration of dual-targeting derivatives for combination therapies, the development of prodrug strategies to improve bioavailability, and the application of computational methods to predict novel bioactive analogs. As understanding of this scaffold's pharmacological potential continues to grow, it is expected to play an increasingly important role in the development of next-generation therapeutics.

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