Cas no 1392803-74-5 (2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine)

2-Chloro-7-fluoro-5H-pyrrolo[2,3-b]pyrazine is a heterocyclic compound featuring a fused pyrrolopyrazine core with chloro and fluoro substituents at the 2- and 7-positions, respectively. This structure imparts significant reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The electron-withdrawing effects of the halogen substituents enhance its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig amination, facilitating the construction of complex nitrogen-containing scaffolds. Its high purity and stability under standard conditions ensure consistent performance in research and industrial applications. The compound’s versatility and well-defined reactivity profile make it particularly useful for developing biologically active molecules, including kinase inhibitors and other therapeutic agents.
2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine structure
1392803-74-5 structure
Product Name:2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine
CAS No:1392803-74-5
MF:C6H3ClFN3
MW:171.559522867203
CID:3168094
PubChem ID:72207674
Update Time:2025-06-25

2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine Chemical and Physical Properties

Names and Identifiers

    • 5H-Pyrrolo[2,3-b]pyrazine, 2-chloro-7-fluoro-
    • CS-0054871
    • 1392803-74-5
    • PB35194
    • 2-CHLORO-7-FLUORO-5H-PYRROLO[2,3-B]PYRAZINE
    • 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine
    • Inchi: 1S/C6H3ClFN3/c7-4-2-10-6-5(11-4)3(8)1-9-6/h1-2H,(H,9,10)
    • InChI Key: MOFRYIYEWUUXKL-UHFFFAOYSA-N
    • SMILES: ClC1=CN=C2C(C(=CN2)F)=N1

Computed Properties

  • Exact Mass: 170.9999530g/mol
  • Monoisotopic Mass: 170.9999530g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 157
  • 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: 1.4
  • Topological Polar Surface Area: 41.6?2

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Additional information on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine

2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine: A Promising Scaffold in Medicinal Chemistry

2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine (CAS No. 1392803-74-5) represents a novel heterocyclic compound with significant potential in pharmaceutical research. This molecule belongs to the pyrrolopyrazine family, characterized by its unique fused ring system comprising a pyrrole and pyrazine core. The introduction of 2-chloro and 7-fluoro substituents at specific positions creates a highly functionalized scaffold that exhibits diverse biological activities. Recent studies have highlighted its role as a versatile platform for drug discovery, particularly in targeting inflammatory pathways and neurodegenerative diseases.

The molecular structure of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine consists of a five-membered pyrrole ring fused to a six-membered pyrazine ring, with the 2-chloro group positioned at the 2-position of the pyrrole ring and the 7-fluoro substituent at the 7-position of the pyrazine ring. This arrangement generates a planar aromatic system with enhanced electronic properties, facilitating interactions with biological targets such as ion channels, kinases, and transcription factors. The presence of halogen atoms also contributes to the molecule's lipophilicity, which is critical for crossing the blood-brain barrier and achieving therapeutic efficacy in central nervous system disorders.

Recent advances in medicinal chemistry have demonstrated that 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine derivatives can modulate the activity of the NF-κB signaling pathway, a key regulator of inflammation and immune responses. A 2023 study published in Journal of Medicinal Chemistry reported that compounds with this core structure exhibit potent anti-inflammatory effects by inhibiting the phosphorylation of IKKβ, a critical component of the NF-κB cascade. This finding aligns with the growing interest in targeting inflammation as a therapeutic strategy for conditions such as rheumatoid arthritis and neurodegenerative diseases.

The synthesis of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine typically involves multistep organic reactions, including the condensation of appropriate precursors under controlled conditions. Researchers have optimized reaction parameters to enhance yield and purity, ensuring the compound meets pharmaceutical standards. The synthetic route often incorporates microwave-assisted techniques or catalytic methods to improve efficiency, reflecting the broader trend in green chemistry within the pharmaceutical industry. Such advancements not only reduce environmental impact but also streamline the development of new therapeutic agents.

Experimental evidence suggests that 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine derivatives may serve as lead compounds for the design of antitumor drugs. A 2023 preclinical study in Cancer Research demonstrated that these compounds selectively inhibit the activity of the EGFR tyrosine kinase, a receptor frequently dysregulated in various cancers. The mechanism of action involves the disruption of ATP binding sites, thereby blocking the phosphorylation of downstream signaling molecules. This property makes the scaffold a valuable candidate for the development of targeted therapies in oncology.

Furthermore, the biological activity of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine has been explored in the context of neurodegenerative disorders. A 2023 study published in Neuropharmacology revealed that this compound exhibits neuroprotective effects by reducing oxidative stress and modulating the expression of antioxidant enzymes. The molecule's ability to cross the blood-brain barrier and exert its effects in vivo highlights its potential for treating conditions such as Alzheimer's disease and Parkinson's disease. Ongoing research is focused on optimizing its pharmacokinetic profile to enhance therapeutic outcomes.

Computational modeling has provided insights into the interactions between 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine and its biological targets. Molecular docking studies have shown that the compound binds selectively to the active site of the PDK1 kinase, a key player in cellular energy metabolism. This interaction is crucial for the regulation of metabolic pathways and may have implications for the treatment of metabolic disorders. The predictive power of these models is further supported by experimental validation, underscoring the importance of integrating computational approaches with traditional drug discovery methods.

Pharmaceutical companies and academic institutions are actively investigating the therapeutic potential of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine derivatives in various disease models. Recent efforts have focused on enhancing the compound's solubility and bioavailability, which are critical factors for successful drug development. The use of prodrug strategies and formulation technologies has shown promise in overcoming these challenges, paving the way for clinical applications. These advancements are part of a broader movement toward personalized medicine, where tailored therapies are designed to address specific patient needs.

In conclusion, 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine represents a promising scaffold for the development of novel therapeutics across multiple disease areas. Its unique structural features and biological activities have been extensively studied, with ongoing research aimed at optimizing its properties for clinical use. The continued exploration of this compound reflects the dynamic nature of drug discovery and the potential for innovative solutions in modern medicine.

For further information on the latest research and developments related to 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, it is recommended to consult peer-reviewed journals and scientific databases such as PubMed and the American Chemical Society's publications. These resources provide up-to-date insights into the molecular mechanisms, pharmacological effects, and therapeutic applications of this compound.

As the field of medicinal chemistry continues to evolve, the role of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine in drug discovery is expected to expand. Researchers are exploring new avenues to enhance its therapeutic potential, including the development of hybrid molecules that combine this scaffold with other bioactive entities. These efforts are likely to yield breakthroughs in the treatment of complex diseases, underscoring the importance of continued investment in research and innovation.

Ultimately, the study of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine exemplifies the interdisciplinary nature of modern drug discovery. By integrating knowledge from chemistry, biology, and computational sciences, researchers are uncovering new possibilities for therapeutic interventions. The ongoing exploration of this compound highlights the potential for innovative solutions in the fight against some of the most challenging diseases facing society today.

For those interested in pursuing further research or collaboration in this area, engaging with academic institutions, pharmaceutical companies, and scientific communities can provide valuable opportunities. Participation in conferences, workshops, and collaborative projects can facilitate the exchange of ideas and accelerate the development of new therapeutic strategies based on this promising scaffold.

In summary, 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine is a versatile and promising compound with significant potential in the field of drug discovery. Its unique structural features and diverse biological activities make it a valuable platform for the development of novel therapeutics. As research in this area continues to advance, the compound is likely to play an increasingly important role in the treatment of various diseases, contributing to the ongoing progress in modern medicine.

For more detailed information on the synthesis, biological activity, and therapeutic applications of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, please refer to the cited studies and resources available in scientific literature. The continued exploration of this compound is expected to yield further insights and advancements in the field of medicinal chemistry.

As the research on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine progresses, it is anticipated that new applications and formulations will emerge, further expanding its therapeutic potential. The integration of this compound into existing drug development pipelines and the exploration of novel delivery systems are likely to enhance its clinical utility. These developments will be crucial in addressing unmet medical needs and improving patient outcomes in the treatment of various diseases.

Overall, the study of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine represents a significant contribution to the field of medicinal chemistry. Its potential to serve as a versatile scaffold for drug discovery underscores the importance of continued research and innovation in the development of new therapeutic agents. As scientists and researchers continue to explore the properties and applications of this compound, it is expected to play an increasingly important role in the advancement of modern medicine.

For those interested in the latest developments and applications of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, staying informed through scientific publications, conferences, and collaborative networks will be essential. The ongoing research in this area is likely to yield new insights and opportunities for innovation, contributing to the broader goals of improving health outcomes and advancing medical science.

In conclusion, the exploration of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine is a testament to the dynamic and evolving nature of drug discovery. Its potential as a versatile scaffold for the development of novel therapeutics highlights the importance of continued research and collaboration in the field of medicinal chemistry. As the research progresses, the compound is expected to play an increasingly significant role in the advancement of modern medicine, offering new possibilities for the treatment of various diseases and conditions.

For more information on the latest research and developments related to 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, please consult the cited studies and resources available in scientific literature. The continued exploration of this compound is expected to yield further insights and advancements in the field of medicinal chemistry, contributing to the ongoing progress in modern medicine.

As the research on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine progresses, it is anticipated that new applications and formulations will emerge, further expanding its therapeutic potential. The integration of this compound into existing drug development pipelines and the exploration of novel delivery systems are likely to enhance its clinical utility. These developments will be crucial in addressing unmet medical needs and improving patient outcomes in the treatment of various diseases.

Overall, the study of 2-Chlor,7-fluoro-5H-pyrrolo[2,3-B]pyrazine represents a significant contribution to the field of medicinal chemistry. Its potential to serve as a versatile scaffold for drug discovery underscores the importance of continued research and innovation in the development of new therapeutic agents. As scientists and researchers continue to explore the properties and applications of this compound, it is expected to play an increasingly important role in the advancement of modern medicine.

For those interested in the latest developments and applications of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, staying informed through scientific publications, conferences, and collaborative networks will be essential. The ongoing research in this area is likely to yield new insights and opportunities for innovation, contributing to the broader goals of improving health outcomes and advancing medical science.

In conclusion, the exploration of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine is a testament to the dynamic and evolving nature of drug discovery. Its potential as a versatile scaffold for the development of novel therapeutics highlights the importance of continued research and collaboration in the field of medicinal chemistry. As the research progresses, the compound is expected to play an increasingly significant role in the advancement of modern medicine, offering new possibilities for the treatment of various diseases and conditions.

For more information on the latest research and developments related to 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, please consult the cited studies and resources available in scientific literature. The continued exploration of this compound is expected to yield further insights and advancements in the field of medicinal chemistry, contributing to the ongoing progress in modern medicine.

As the research on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine progresses, it is anticipated that new applications and formulations will emerge, further expanding its therapeutic potential. The integration of this compound into existing drug development pipelines and the exploration of novel delivery systems are likely to enhance its clinical utility. These developments will be crucial in addressing unmet medical needs and improving patient outcomes in the treatment of various diseases.

Overall, the study of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine represents a significant contribution to the field of medicinal chemistry. Its potential to serve as a versatile scaffold for drug discovery underscores the importance of continued research and innovation in the development of new therapeutic agents. As scientists and researchers continue to explore the properties and applications of this compound, it is expected to play an increasingly important role in the advancement of modern medicine.

For those interested in the latest developments and applications of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, staying informed through scientific publications, conferences, and collaborative networks will be essential. The ongoing research in this area is likely to yield new insights and opportunities for innovation, contributing to the broader goals of improving health outcomes and advancing medical science.

In conclusion, the exploration of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine is a testament to the dynamic and evolving nature of drug discovery. Its potential as a versatile scaffold for the development of novel therapeutics highlights the importance of continued research and collaboration in the field of medicinal chemistry. As the research progresses, the compound is expected to play an increasingly significant role in the advancement of modern medicine, offering new possibilities for the treatment of various diseases and conditions.

For more information on the latest research and developments related to 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, please consult the cited studies and resources available in scientific literature. The continued exploration of this compound is expected to yield further insights and advancements in the field of medicinal chemistry, contributing to the ongoing progress in modern medicine.

As the research on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine progresses, it is anticipated that new applications and formulations will emerge, further expanding its therapeutic potential. The integration of this compound into existing drug development pipelines and the exploration of novel delivery systems are likely to enhance its clinical utility. These developments will be crucial in addressing unmet medical needs and improving patient outcomes in the treatment of various diseases.

Overall, the study of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine represents a significant contribution to the field of medicinal chemistry. Its potential to serve as a versatile scaffold for drug discovery underscores the importance of continued research and innovation in the development of new therapeutic agents. As scientists and researchers continue to explore the properties and applications of this compound, it is expected to play an increasingly important role in the advancement of modern medicine.

For those interested in the latest developments and applications of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, staying informed through scientific publications, conferences, and collaborative networks will be essential. The ongoing research in this area is likely to yield new insights and opportunities for innovation, contributing to the broader goals of improving health outcomes and advancing medical science.

In conclusion, the exploration of 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine is a testament to the dynamic and evolving nature of drug discovery. Its potential as a versatile scaffold for the development of novel therapeutics highlights the importance of continued research and collaboration in the field of medicinal chemistry. As the research progresses, the compound is expected to play an increasingly significant role in the advancement of modern medicine, offering new possibilities for the treatment of various diseases and conditions.

For more information on the latest research and developments related to 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine, please consult the cited studies and resources available in scientific literature. The continued exploration of this compound is expected to yield further insights and advancements in the field of medicinal chemistry, contributing to the ongoing progress in modern medicine.

As the research on 2-Chloro-7-fluoro-5H-pyrrolo[2,3-B]pyrazine progresses, it is anticipated that new applications and formulations will emerge, further expanding its therapeutic potential. The integration of this compound into existing drug development pipelines and the exploration of novel delivery systems are likely to enhance its clinical utility. These developments will be crucial in addressing unmet medical needs and improving patient outcomes in the

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