Cas no 954217-58-4 (ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate)

Ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate is a brominated heterocyclic compound featuring an imidazopyridine core with an ester functional group. This intermediate is valuable in medicinal chemistry and pharmaceutical research due to its versatility in further functionalization, particularly in Suzuki-Miyaura and other cross-coupling reactions. The bromine substituent at the 6-position enhances reactivity for nucleophilic aromatic substitution, while the ethyl ester group allows for straightforward hydrolysis or transesterification. Its rigid fused-ring structure contributes to its utility in designing bioactive molecules, including kinase inhibitors and other therapeutic agents. The compound is typically handled under inert conditions to ensure stability and purity.
ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate structure
954217-58-4 structure
Product Name:ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate
CAS No:954217-58-4
MF:C9H8BrN3O2
MW:270.082720756531
CID:2157463
PubChem ID:22308599
Update Time:2025-06-11

ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-1h-imidazo[4,5-b]pyridine-2-carboxylic acid ethyl ester
    • ethyl 6-bromo-1H-imidazo[4,5-b]pyridine-2-carboxylate
    • ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate
    • MFCD19441298
    • SCHEMBL20552713
    • SY352039
    • AKOS012662531
    • 954217-58-4
    • DB-253504
    • MDL: MFCD19441298
    • Inchi: 1S/C9H8BrN3O2/c1-2-15-9(14)8-12-6-3-5(10)4-11-7(6)13-8/h3-4H,2H2,1H3,(H,11,12,13)
    • InChI Key: NJZUANIECDYRNO-UHFFFAOYSA-N
    • SMILES: BrC1C=NC2=C(C=1)NC(C(=O)OCC)=N2

Computed Properties

  • Exact Mass: 268.97999Da
  • Monoisotopic Mass: 268.97999Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 252
  • 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
  • Topological Polar Surface Area: 67.9?2

ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate Pricemore >>

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Additional information on ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate

Recent Advances in the Study of Ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate (CAS: 954217-58-4)

Ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate (CAS: 954217-58-4) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential applications in drug discovery and development. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly those targeting kinase inhibition and other therapeutic pathways. Recent studies have explored its utility in the design of novel pharmaceuticals, highlighting its versatility and importance in modern drug research.

One of the most notable applications of ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate is its role in the synthesis of kinase inhibitors. Kinases are critical enzymes involved in signal transduction pathways, and their dysregulation is often associated with diseases such as cancer, inflammation, and neurodegenerative disorders. Researchers have utilized this compound as a scaffold to develop potent and selective inhibitors for kinases like JAK2, ALK, and EGFR, which are prominent targets in oncology. The bromo-substitution at the 6-position allows for further functionalization, enabling the introduction of diverse pharmacophores to enhance binding affinity and selectivity.

In a recent study published in the Journal of Medicinal Chemistry, scientists demonstrated the efficacy of derivatives synthesized from ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate in inhibiting tumor growth in vitro and in vivo. The study employed structure-activity relationship (SAR) analysis to optimize the compound's pharmacokinetic properties, resulting in derivatives with improved bioavailability and reduced off-target effects. These findings underscore the compound's potential as a lead structure for the development of next-generation anticancer agents.

Another area of interest is the use of ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate in the synthesis of small-molecule modulators for neurodegenerative diseases. Recent research has shown that imidazopyridine derivatives can cross the blood-brain barrier and exhibit neuroprotective effects. For instance, a study in ACS Chemical Neuroscience reported that analogs of this compound demonstrated significant activity in reducing amyloid-beta aggregation, a hallmark of Alzheimer's disease. This opens new avenues for the development of therapeutics targeting protein misfolding disorders.

Beyond its therapeutic applications, ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate has also been explored in materials science. Its unique electronic properties make it a candidate for the development of organic semiconductors and fluorescent probes. Researchers have synthesized conjugated polymers incorporating this moiety, which exhibit tunable luminescence and charge transport characteristics. Such materials hold promise for applications in optoelectronic devices and bioimaging.

In conclusion, ethyl 6-bromo-3H-imidazo[4,5-b]pyridine-2-carboxylate (CAS: 954217-58-4) continues to be a versatile and valuable compound in chemical biology and medicinal chemistry. Its applications span from drug discovery to materials science, driven by its adaptable chemical structure and functionalizability. Ongoing research is expected to further elucidate its potential and expand its utility in addressing unmet medical and technological challenges.

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