Cas no 936470-68-7 (4-Hydroxy-7-methoxy-6-azaindole)

4-Hydroxy-7-methoxy-6-azaindole is a heterocyclic organic compound featuring a fused azaindole core with hydroxyl and methoxy functional groups at the 4- and 7-positions, respectively. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its azaindole scaffold is particularly relevant in medicinal chemistry due to its bioisosteric resemblance to indole, enhancing binding affinity and metabolic stability in drug candidates. The compound's functional groups also offer versatile reactivity for further derivatization. High purity and well-defined synthetic routes ensure reproducibility for research and industrial applications, particularly in the development of kinase inhibitors and other biologically active molecules.
4-Hydroxy-7-methoxy-6-azaindole structure
936470-68-7 structure
Product Name:4-Hydroxy-7-methoxy-6-azaindole
CAS No:936470-68-7
MF:C8H8N2O2
MW:164.161321640015
CID:827187
PubChem ID:29981172
Update Time:2025-10-29

4-Hydroxy-7-methoxy-6-azaindole Chemical and Physical Properties

Names and Identifiers

    • 4-Hydroxy-7-methoxy-6-azaindole
    • 7-methoxy-1H-pyrrolo[2,3-c]pyridin-4-ol
    • FT-0658590
    • FT-0669381
    • 936470-68-7
    • AKOS006312104
    • DTXSID60652600
    • Inchi: 1S/C8H8N2O2/c1-12-8-7-5(2-3-9-7)6(11)4-10-8/h2-4,9,11H,1H3
    • InChI Key: LKUWKIKHLJCCNZ-UHFFFAOYSA-N
    • SMILES: O(C)C1C2=C(C(=CN=1)O)C=CN2

Computed Properties

  • Exact Mass: 164.05900
  • Monoisotopic Mass: 164.058577502g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 165
  • 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
  • Surface Charge: 0
  • Tautomer Count: 8
  • XLogP3: 0.9
  • Topological Polar Surface Area: 58.1?2

Experimental Properties

  • Density: 1.396
  • Boiling Point: 506.8°C at 760 mmHg
  • Flash Point: 260.3°C
  • Refractive Index: 1.695
  • PSA: 58.14000
  • LogP: 1.27710

4-Hydroxy-7-methoxy-6-azaindole Pricemore >>

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Additional information on 4-Hydroxy-7-methoxy-6-azaindole

Introduction to 4-Hydroxy-7-methoxy-6-azaindole (CAS No. 936470-68-7) and Its Emerging Applications in Chemical Biology

4-Hydroxy-7-methoxy-6-azaindole (CAS No. 936470-68-7) is a heterocyclic compound that has garnered significant attention in the field of chemical biology due to its unique structural properties and potential biological activities. This compound belongs to the azaindole family, a class of molecules characterized by a nitrogen atom incorporated into the indole scaffold, which often confers enhanced binding affinity and selectivity in biological targets. The presence of both hydroxyl and methoxy substituents in its structure further modulates its pharmacophoric features, making it a promising candidate for drug discovery and therapeutic development.

The chemical structure of 4-Hydroxy-7-methoxy-6-azaindole consists of a benzene ring fused with a pyrrole ring, with the nitrogen atom replacing one of the carbon atoms in the indole core. The hydroxyl group at the 4-position and the methoxy group at the 7-position introduce polar functionalities that can interact with biological targets through hydrogen bonding and other non-covalent interactions. This structural motif has been extensively studied for its potential applications in medicinal chemistry, particularly in the design of small-molecule inhibitors targeting enzymes and receptors involved in various disease pathways.

In recent years, 4-Hydroxy-7-methoxy-6-azaindole has been explored as a key intermediate in the synthesis of bioactive molecules. Its versatility as a building block allows for modifications at multiple positions, enabling chemists to tailor its properties for specific biological applications. One notable area of interest is its use in developing inhibitors of kinases, which are enzymes implicated in cancer progression and other inflammatory diseases. The nitrogen-containing heterocycle enhances binding interactions with the ATP-binding pockets of kinases, leading to potent inhibition of their activity.

Recent studies have highlighted the potential of 4-Hydroxy-7-methoxy-6-azaindole derivatives as scaffolds for antiviral agents. The compound’s ability to interfere with viral replication cycles by inhibiting key viral enzymes has been demonstrated in preclinical models. For instance, modifications at the 5-position of the azaindole core have been shown to enhance antiviral activity against RNA viruses by disrupting viral polymerase function. This research underscores the importance of 4-Hydroxy-7-methoxy-6-azaindole as a versatile platform for developing novel therapeutics against emerging infectious diseases.

The pharmacokinetic properties of 4-Hydroxy-7-methoxy-6-azaindole have also been thoroughly investigated. Its solubility, metabolic stability, and distribution profiles make it an attractive candidate for oral administration. Studies have shown that derivatives of this compound exhibit favorable pharmacokinetic profiles in animal models, suggesting their potential for clinical translation. Furthermore, computational modeling has been employed to optimize its structure for improved bioavailability and reduced toxicity, further solidifying its position as a promising lead compound.

Another area where 4-Hydroxy-7-methoxy-6-azaindole has shown promise is in the development of neuroprotective agents. Neurodegenerative diseases such as Alzheimer’s and Parkinson’s are characterized by protein misfolding and aggregation, leading to neuronal dysfunction. Compounds derived from 4-Hydroxy-7-methoxy-6-azaindole have demonstrated the ability to inhibit aggregation by interacting with misfolded proteins, thereby protecting neurons from oxidative stress and apoptosis. This mechanism has opened new avenues for therapeutic intervention in neurodegenerative disorders.

The synthesis of 4-Hydroxy-7-methoxy-6-azaindole involves multi-step organic reactions that highlight its synthetic utility. Modern synthetic methodologies have enabled efficient access to this compound via catalytic processes that minimize waste and improve yield. Advances in flow chemistry have further streamlined its production, making it more accessible for large-scale applications in drug discovery programs. These advancements underscore the importance of 4-Hydroxy-7-methoxy-6-azaindole as a cornerstone molecule in synthetic organic chemistry.

The role of 4-Hydroxy-7-methoxy-6-azaindole in medicinal chemistry extends beyond kinase inhibition and antiviral applications. It has been explored as a scaffold for developing compounds targeting other disease pathways, including cancer metabolism and immune modulation. By leveraging its structural flexibility, researchers have designed molecules that disrupt metabolic pathways essential for tumor growth or enhance immune responses against cancer cells. These findings highlight the broad therapeutic potential of 4-Hydroxy-7-methoxy-6-azaindole derivatives.

In conclusion, 4-Hydroxy-7-methoxy-6 azaindole (CAS No: 93647068 7) represents a structurally intriguing compound with significant promise in chemical biology and drug discovery. Its unique pharmacophoric features make it an excellent candidate for developing novel therapeutics targeting various diseases, including cancer, viral infections, and neurodegenerative disorders. The ongoing research into its derivatives continues to uncover new applications, reinforcing its importance as a key molecule in modern medicinal chemistry.

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