Cas no 1823374-98-6 (7-bromo-6-chloropyrido[2,3-b]pyrazine)

7-Bromo-6-chloropyrido[2,3-b]pyrazine is a heterocyclic compound featuring a pyrido[2,3-b]pyrazine core substituted with bromine and chlorine at the 7- and 6-positions, respectively. This structure imparts reactivity suitable for further functionalization, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The presence of halogen substituents enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling the construction of complex nitrogen-containing scaffolds. Its high purity and stability under standard conditions ensure consistent performance in synthetic applications. Researchers favor this compound for its versatility in medicinal chemistry, particularly in the development of kinase inhibitors and other biologically active molecules.
7-bromo-6-chloropyrido[2,3-b]pyrazine structure
1823374-98-6 structure
Product Name:7-bromo-6-chloropyrido[2,3-b]pyrazine
CAS No:1823374-98-6
MF:C7H3BrClN3
MW:244.475818872452
CID:5843489
PubChem ID:92132891
Update Time:2025-06-14

7-bromo-6-chloropyrido[2,3-b]pyrazine Chemical and Physical Properties

Names and Identifiers

    • 7-bromo-6-chloropyrido[2,3-b]pyrazine
    • Pyrido[2,3-b]pyrazine, 7-bromo-6-chloro-
    • 1823374-98-6
    • EN300-7950007
    • Inchi: 1S/C7H3BrClN3/c8-4-3-5-7(12-6(4)9)11-2-1-10-5/h1-3H
    • InChI Key: XRVLIAZLPDGRHR-UHFFFAOYSA-N
    • SMILES: C12=NC(Cl)=C(Br)C=C1N=CC=N2

Computed Properties

  • Exact Mass: 242.91989g/mol
  • Monoisotopic Mass: 242.91989g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 169
  • 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: 2.1
  • Topological Polar Surface Area: 38.7?2

Experimental Properties

  • Density: 1.861±0.06 g/cm3(Predicted)
  • Boiling Point: 329.3±37.0 °C(Predicted)
  • pka: -3.15±0.30(Predicted)

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Additional information on 7-bromo-6-chloropyrido[2,3-b]pyrazine

Recent Advances in the Study of 7-bromo-6-chloropyrido[2,3-b]pyrazine (CAS: 1823374-98-6)

The compound 7-bromo-6-chloropyrido[2,3-b]pyrazine (CAS: 1823374-98-6) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential as a versatile scaffold for drug discovery. This heterocyclic compound, characterized by its pyrido[2,3-b]pyrazine core, has been explored for its ability to interact with various biological targets, making it a promising candidate for the development of novel therapeutics. Recent studies have focused on its synthesis, structural modifications, and biological evaluations, shedding light on its pharmacological properties and potential applications.

One of the key areas of research involving 7-bromo-6-chloropyrido[2,3-b]pyrazine is its role as a building block in the synthesis of kinase inhibitors. Kinases are critical regulators of cellular signaling pathways, and their dysregulation is implicated in numerous diseases, including cancer and inflammatory disorders. Researchers have utilized the bromo and chloro substituents on the pyrido[2,3-b]pyrazine ring to introduce further functional groups, enabling the development of highly selective and potent kinase inhibitors. Recent publications highlight the compound's utility in targeting specific kinases, such as JAK2 and EGFR, with improved efficacy and reduced off-target effects.

In addition to its applications in kinase inhibition, 7-bromo-6-chloropyrido[2,3-b]pyrazine has been investigated for its potential in antimicrobial therapy. A study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The mechanism of action appears to involve disruption of bacterial cell wall synthesis, a finding that could pave the way for new antibiotics in an era of increasing antimicrobial resistance.

Another notable advancement is the use of 7-bromo-6-chloropyrido[2,3-b]pyrazine in the development of fluorescent probes for biological imaging. Researchers have exploited the compound's unique electronic properties to design probes that can selectively bind to cellular targets, enabling real-time visualization of biological processes. This application has significant implications for both basic research and clinical diagnostics, offering new tools for studying disease mechanisms at the molecular level.

Despite these promising developments, challenges remain in the optimization of 7-bromo-6-chloropyrido[2,3-b]pyrazine-based compounds. Issues such as solubility, bioavailability, and metabolic stability need to be addressed to translate these findings into clinically viable therapeutics. Ongoing research is focused on structural optimization and formulation strategies to overcome these hurdles, with several candidates currently in preclinical evaluation.

In conclusion, 7-bromo-6-chloropyrido[2,3-b]pyrazine (CAS: 1823374-98-6) represents a highly versatile scaffold with broad applications in drug discovery and chemical biology. Recent studies have underscored its potential in kinase inhibition, antimicrobial therapy, and biological imaging, highlighting its value as a tool for both research and therapeutic development. As research continues, this compound is likely to play an increasingly important role in addressing unmet medical needs and advancing our understanding of complex biological systems.

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