Cas no 1159829-63-6 (4-Bromo-1H-pyrazolo[4,3-c]pyridine)

4-Bromo-1H-pyrazolo[4,3-c]pyridine structure
1159829-63-6 structure
Product Name:4-Bromo-1H-pyrazolo[4,3-c]pyridine
CAS No:1159829-63-6
MF:C6H4BrN3
MW:198.020059585571
MDL:MFCD12401001
CID:1205273
PubChem ID:71307617
Update Time:2025-07-24

4-Bromo-1H-pyrazolo[4,3-c]pyridine Chemical and Physical Properties

Names and Identifiers

    • 4-bromo-1h-pyrazolo[4,3-c]pyridine
    • 1H-Pyrazolo[4,3-c]pyridine, 4-broMo-
    • AK165330
    • 4-Bromo-5-azaindazole
    • 1h-pyrazolo[4,3-c]pyridine,4-bromo-
    • PB28426
    • FCH1159133
    • ST1221273
    • AX8320767
    • AB0037883
    • Y5216
    • SCHEMBL20595731
    • 1159829-63-6
    • 4-bromo-2H-pyrazolo[4,3-c]pyridine
    • AKOS024015492
    • EN300-3193299
    • DTXSID70745411
    • SY069197
    • CS-0051011
    • AS-30632
    • A893695
    • DA-19317
    • SCHEMBL26116145
    • MFCD12401001
    • 4-Bromo-1H-pyrazolo[4,3-c]pyridine
    • MDL: MFCD12401001
    • Inchi: 1S/C6H4BrN3/c7-6-4-3-9-10-5(4)1-2-8-6/h1-3H,(H,9,10)
    • InChI Key: OPTKCRUGKAZNCI-UHFFFAOYSA-N
    • SMILES: BrC1C2C=NNC=2C=CN=1

Computed Properties

  • Exact Mass: 196.95886g/mol
  • Monoisotopic Mass: 196.95886g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 130
  • 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: 41.6
  • XLogP3: 1.5

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Additional information on 4-Bromo-1H-pyrazolo[4,3-c]pyridine

Recent Advances in the Application of 4-Bromo-1H-pyrazolo[4,3-c]pyridine (CAS: 1159829-63-6) in Chemical Biology and Pharmaceutical Research

The compound 4-Bromo-1H-pyrazolo[4,3-c]pyridine (CAS: 1159829-63-6) has recently emerged as a key scaffold in medicinal chemistry and chemical biology due to its versatile reactivity and potential therapeutic applications. This heterocyclic structure, characterized by a pyrazolo[4,3-c]pyridine core with a bromine substituent at the 4-position, serves as a privileged building block for the synthesis of bioactive molecules. Recent studies have highlighted its utility in targeting protein kinases, modulating enzymatic activity, and serving as a precursor for fluorescent probes in cellular imaging.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of 4-Bromo-1H-pyrazolo[4,3-c]pyridine derivatives as selective inhibitors of JAK3 kinase, a critical target in autoimmune diseases. The researchers utilized structure-activity relationship (SAR) analysis to optimize the bromo-substituted scaffold, achieving nanomolar potency while maintaining excellent selectivity over other JAK family members. The lead compound, derived from this scaffold, showed promising results in preclinical models of rheumatoid arthritis, with reduced off-target effects compared to existing therapeutics.

In parallel research, scientists have explored the photophysical properties of 4-Bromo-1H-pyrazolo[4,3-c]pyridine derivatives for bioimaging applications. A recent publication in ACS Chemical Biology reported the development of a novel fluorescent probe based on this scaffold, which exhibits exceptional photostability and membrane permeability. The probe's bromine atom serves as an ideal handle for further functionalization through palladium-catalyzed cross-coupling reactions, enabling the creation of targeted imaging agents for specific cellular compartments.

The synthetic accessibility of 4-Bromo-1H-pyrazolo[4,3-c]pyridine has also been improved through recent methodological advances. A 2024 Nature Protocols article detailed a streamlined, high-yielding synthesis of this compound and its derivatives using continuous flow chemistry techniques. This approach significantly reduces reaction times and improves scalability, addressing previous challenges in large-scale production. The protocol emphasizes the importance of the bromine substituent in facilitating downstream diversification through various cross-coupling reactions.

Emerging applications in targeted protein degradation have further expanded the utility of this scaffold. Researchers have successfully incorporated 4-Bromo-1H-pyrazolo[4,3-c]pyridine into proteolysis-targeting chimeras (PROTACs), leveraging its ability to form stable interactions with E3 ubiquitin ligases. Preliminary data suggest these novel degraders exhibit improved pharmacokinetic properties compared to traditional small-molecule inhibitors, particularly in overcoming drug resistance mechanisms.

As the field progresses, computational studies have provided deeper insights into the molecular interactions of 4-Bromo-1H-pyrazolo[4,3-c]pyridine-containing compounds. Advanced molecular dynamics simulations and free energy calculations have revealed unique binding modes that explain the scaffold's selectivity profiles. These computational tools are now being employed to design next-generation derivatives with enhanced potency and reduced toxicity.

The growing body of research on 4-Bromo-1H-pyrazolo[4,3-c]pyridine (CAS: 1159829-63-6) underscores its importance as a multifunctional scaffold in drug discovery and chemical biology. Future directions include exploring its applications in covalent inhibitor design, the development of bifunctional chemical probes, and the creation of novel materials for biomedical applications. The compound's versatility and the recent methodological advances in its synthesis and modification position it as a valuable tool for addressing current challenges in pharmaceutical research.

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