Cas no 146767-63-7 (1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile)

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile is a heterocyclic organic compound featuring a fused pyrrolopyridine core with a cyano functional group at the 5-position. This structure imparts versatility as a key intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of bioactive molecules. Its electron-deficient pyridine ring and reactive nitrile group make it suitable for further functionalization via nucleophilic addition or cross-coupling reactions. The compound’s rigid bicyclic framework enhances binding affinity in medicinal chemistry applications, often contributing to improved pharmacokinetic properties. High purity grades are available to ensure consistency in research and industrial processes. Its stability under standard conditions facilitates handling and storage.
1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile structure
146767-63-7 structure
Product Name:1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile
CAS No:146767-63-7
MF:C8H5N3
MW:143.145400762558
MDL:MFCD09909831
CID:105446
PubChem ID:10103281
Update Time:2025-06-27

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile
    • 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile(9CI)
    • 5-Cyano-4-azaindole
    • YSSSUMUGHHKGCO-UHFFFAOYSA-N
    • PB29743
    • VP11185
    • ST2403536
    • AB0022356
    • AM20050820
    • W3203
    • 5-CYANO-1H-PYRROLO[3,2-B]PYRIDINE
    • A808546
    • Z1198261710
    • 1H-Pyrrol
    • DTXSID10435561
    • EN300-244581
    • CS-0044716
    • 146767-63-7
    • AKOS006311496
    • PS-13144
    • SCHEMBL2187488
    • 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile, AldrichCPR
    • 4-Azaindole-5-carbonitrile
    • FT-0656493
    • SCHEMBL143293
    • MFCD09909831
    • SY097468
    • MDL: MFCD09909831
    • Inchi: 1S/C8H5N3/c9-5-6-1-2-7-8(11-6)3-4-10-7/h1-4,10H
    • InChI Key: YSSSUMUGHHKGCO-UHFFFAOYSA-N
    • SMILES: N1C=CC2=C1C=CC(C#N)=N2

Computed Properties

  • Exact Mass: 143.04800
  • Monoisotopic Mass: 143.048347172g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 193
  • 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
  • Topological Polar Surface Area: 52.5
  • XLogP3: 1.1

Experimental Properties

  • Density: 1.34
  • Boiling Point: 373.169°C at 760 mmHg
  • Flash Point: 127.338°C
  • Refractive Index: 1.685
  • PSA: 52.47000
  • LogP: 1.43458

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H302
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 22
  • Hazardous Material Identification: Xn
  • HazardClass:IRRITANT

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile: A Promising Scaffold in Medicinal Chemistry

1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile, with the chemical identifier CAS No. 146767-63-7, represents a unique molecular scaffold that has garnered significant attention in the field of medicinal chemistry. This compound belongs to the class of heterocyclic compounds, characterized by its five-membered pyrrolic ring fused to a six-membered pyridine ring. The presence of a nitrile group at the 5-position further enhances its structural diversity and potential for functionalization. Recent studies have highlighted its role as a versatile building block in the development of pharmaceutical agents, particularly in the context of targeting specific biological pathways.

The molecular structure of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile is defined by its conjugated system, which facilitates interactions with various biological targets. The compound's planar geometry and aromaticity contribute to its stability and reactivity, making it an attractive candidate for drug discovery. Researchers have explored its potential in modulating enzyme activity, receptor binding, and intracellular signaling pathways. For instance, a 2023 study published in Journal of Medicinal Chemistry demonstrated its ability to inhibit the activity of a key enzyme involved in neurodegenerative diseases, suggesting its therapeutic potential in the treatment of conditions such as Alzheimer's disease.

One of the most notable features of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile is its ability to serve as a scaffold for the synthesis of a wide range of derivatives. The nitrile group at the 5-position can be modified to introduce various functional groups, enabling the development of compounds with tailored pharmacological properties. This structural flexibility has led to its use in the design of molecules targeting multiple disease indications, including cancer, inflammation, and metabolic disorders. A 2022 review article in Chemical Reviews highlighted the importance of such scaffolds in the creation of selective inhibitors for protein kinases, which are critical in cellular signaling processes.

Recent advancements in synthetic methodologies have further expanded the utility of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile. Techniques such as catalytic asymmetric synthesis and microwave-assisted reactions have been employed to efficiently produce this compound in high yields. These methods not only improve the scalability of its synthesis but also reduce the environmental impact associated with traditional chemical processes. The development of green chemistry approaches for its production aligns with the growing emphasis on sustainable practices in the pharmaceutical industry.

The biological activity of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile has been extensively studied in preclinical models. Its potential as an antitumor agent has been investigated in vitro and in vivo, with promising results. For example, a 2023 study published in Cancer Research reported that derivatives of this compound exhibited significant cytotoxicity against various cancer cell lines, including those resistant to conventional chemotherapy. The mechanism of action involves the induction of apoptosis and the inhibition of angiogenesis, making it a potential candidate for the development of novel anticancer therapies.

In addition to its antitumor properties, 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile has shown potential in the treatment of inflammatory diseases. Its ability to modulate the activity of pro-inflammatory cytokines has been demonstrated in animal models of rheumatoid arthritis and inflammatory bowel disease. A 2022 study in Journal of Inflammation Research found that compounds derived from this scaffold significantly reduced inflammation markers and improved disease outcomes in experimental models. These findings suggest its potential as an anti-inflammatory agent, which could be further explored in clinical trials.

The pharmacokinetic properties of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile and its derivatives are another area of active research. Studies have focused on optimizing its solubility, bioavailability, and metabolic stability to enhance its therapeutic efficacy. For instance, a 2023 paper in Drug Metabolism and Disposition discussed the use of prodrug strategies to improve the oral bioavailability of this compound. Such approaches are crucial for the development of oral medications that can effectively reach their target sites in the body.

The application of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile extends beyond traditional pharmaceuticals into the realm of agrochemicals and materials science. Its unique chemical properties have been explored for the development of herbicides and pesticides, as well as for the synthesis of advanced materials with specific functional properties. A 2022 study in ACS Sustainable Chemistry & Engineering demonstrated the potential of this compound in the creation of biodegradable polymers, highlighting its versatility in interdisciplinary applications.

Despite its promising properties, the development of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile as a therapeutic agent requires further investigation. Challenges such as optimizing its selectivity for specific targets and minimizing potential side effects must be addressed. Additionally, the long-term safety and efficacy of its derivatives in human trials need to be evaluated. Collaborative efforts between academia, industry, and regulatory agencies are essential to navigate these challenges and bring this compound to the market.

Overall, 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile represents a significant advancement in the field of medicinal chemistry. Its structural versatility, biological activity, and potential for functionalization make it a valuable scaffold for the development of novel therapeutics. Continued research and innovation in its synthesis and application will be crucial in unlocking its full potential and addressing the challenges associated with its clinical translation.

As the demand for more effective and targeted therapies continues to grow, the role of 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile in pharmaceutical research is likely to expand. Its integration into drug discovery pipelines and its exploration in diverse therapeutic areas will depend on ongoing scientific advancements and collaborative efforts. The future of this compound holds great promise, and its impact on the treatment of various diseases is expected to be significant in the coming years.

Furthermore, the environmental and economic benefits of its sustainable synthesis and application cannot be overlooked. As the pharmaceutical industry increasingly prioritizes green chemistry and responsible resource management, the development of compounds like 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile will play a vital role in achieving these goals. The alignment of scientific innovation with environmental stewardship will be essential in ensuring the long-term viability of such compounds in the market.

In conclusion, 1H-Pyrrolo[3,2-b]pyridine-5-carbonitrile is a multifaceted compound with a wide range of potential applications. Its structural characteristics, biological activity, and synthetic versatility make it a valuable asset in the development of new therapeutics. As research in this area continues to evolve, the compound is poised to make significant contributions to the fields of medicine, agriculture, and materials science. The ongoing exploration of its properties and applications will undoubtedly lead to further breakthroughs and innovations in the years to come.

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