Cas no 1202179-41-6 (7-bromo-2-ethyl-imidazo[1,2-a]pyridine)

7-Bromo-2-ethyl-imidazo[1,2-a]pyridine is a heterocyclic compound featuring a bromine substituent at the 7-position and an ethyl group at the 2-position of the imidazo[1,2-a]pyridine scaffold. This structure imparts reactivity suitable for further functionalization, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The bromine moiety enables cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the introduction of diverse substituents. The ethyl group enhances lipophilicity, potentially improving bioavailability in drug development. Its well-defined synthetic route and stability under standard conditions ensure consistent quality for research and industrial applications. This compound is particularly useful in medicinal chemistry for the design of bioactive molecules targeting CNS and inflammatory pathways.
7-bromo-2-ethyl-imidazo[1,2-a]pyridine structure
1202179-41-6 structure
Product Name:7-bromo-2-ethyl-imidazo[1,2-a]pyridine
CAS No:1202179-41-6
MF:C9H9BrN2
MW:225.085160970688
CID:1209195
PubChem ID:67027413
Update Time:2025-10-31

7-bromo-2-ethyl-imidazo[1,2-a]pyridine Chemical and Physical Properties

Names and Identifiers

    • 7-bromo-2-ethyl-imidazo[1,2-a]pyridine
    • 7-bromo-2-ethylimidazo[1,2-a]pyridine
    • EN300-1197866
    • DB-399951
    • SCHEMBL1426874
    • 1202179-41-6
    • Inchi: 1S/C9H9BrN2/c1-2-8-6-12-4-3-7(10)5-9(12)11-8/h3-6H,2H2,1H3
    • InChI Key: ULRKPCDDQOTHNA-UHFFFAOYSA-N
    • SMILES: BrC1C=CN2C=C(CC)N=C2C=1

Computed Properties

  • Exact Mass: 223.99491g/mol
  • Monoisotopic Mass: 223.99491g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 163
  • 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: 3.3
  • Topological Polar Surface Area: 17.3?2

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Additional information on 7-bromo-2-ethyl-imidazo[1,2-a]pyridine

Professional Introduction to 7-bromo-2-ethyl-imidazo[1,2-a]pyridine (CAS No: 1202179-41-6)

7-bromo-2-ethyl-imidazo[1,2-a]pyridine, with the chemical identifier CAS No: 1202179-41-6, is a significant compound in the field of pharmaceutical chemistry. This heterocyclic compound belongs to the imidazopyridine class, which has garnered considerable attention due to its versatile applications in drug discovery and medicinal chemistry. The structural features of 7-bromo-2-ethyl-imidazo[1,2-a]pyridine make it a valuable intermediate in the synthesis of various bioactive molecules, particularly those targeting neurological and inflammatory disorders.

The< strong>imidozopyridine core of this compound contributes to its unique pharmacological properties. Imidazopyridines are known for their ability to interact with multiple biological targets, including receptors and enzymes involved in pain perception, immune responses, and central nervous system (CNS) functions. Recent studies have highlighted the potential of< strong>7-bromo-2-ethyl-imidazo[1,2-a]pyridine as a scaffold for developing novel therapeutic agents. Its brominated and ethyl-substituted structure provides ample opportunities for further functionalization, enabling the creation of derivatives with enhanced binding affinity and selectivity.

In the realm of drug development, the< strong>CAS No: 1202179-41-6 compound has been explored for its role in modulating inflammatory pathways. Chronic inflammation is a hallmark of numerous diseases, including arthritis, atherosclerosis, and certain types of cancer. Preclinical research indicates that< strong>7-bromo-2-ethyl-imidazo[1,2-a]pyridine can interfere with key inflammatory mediators by inhibiting the production of pro-inflammatory cytokines. This mechanism has sparked interest in its potential as an anti-inflammatory agent, particularly in conditions where traditional therapies have limited efficacy.

The< strong>bromine substituent at the 7-position of the imidazopyridine ring is particularly noteworthy. Bromine atoms are often employed in medicinal chemistry due to their ability to enhance metabolic stability and binding interactions with biological targets. In< strong>7-bromo-2-ethyl-imidazo[1,2-a]pyridine, this bromine atom serves as a handle for further chemical modifications, allowing researchers to fine-tune the compound's pharmacokinetic profile. For instance, palladium-catalyzed cross-coupling reactions can be utilized to introduce diverse functional groups at the brominated position, thereby expanding the chemical space for drug discovery.

Recent advancements in computational chemistry have further illuminated the therapeutic potential of< strong>CAS No: 1202179-41-6. Molecular docking studies have demonstrated that this compound can bind effectively to various protein targets associated with neurological disorders. For example, it has shown promise in interacting with sigma-1 receptors, which are implicated in conditions such as Alzheimer's disease and epilepsy. The< strong>ethyl group at the 2-position of the imidazopyridine ring appears to play a crucial role in optimizing these interactions, contributing to improved receptor affinity and selectivity.

The synthesis of< strong>7-bromo-2-ethyl-imidazo[1,2-a]pyridine involves multi-step organic transformations that highlight its synthetic utility. Starting from commercially available precursors, such as 2-aminoimidazole and 3-bromopropene, the compound can be constructed through sequential condensation reactions followed by bromination and alkylation steps. This synthetic route underscores the feasibility of large-scale production, making it accessible for both academic research and industrial applications.

The pharmacological evaluation of< strong>CAS No: 1202179-41-6 has revealed intriguing findings regarding its biological activity. In vitro assays have shown that it exhibits moderate potency against certain cancer cell lines by inhibiting key signaling pathways involved in tumor growth and survival. Specifically, it has been observed to disrupt the activity of cyclin-dependent kinases (CDKs), which are critical regulators of cell cycle progression. These findings suggest that< strong>7-bromo-2-ethyl-imidazo[1,2-a]pyridine could serve as a lead compound for developing novel anticancer agents.

The< strong>brominated imidazopyridine scaffold also holds promise for applications beyond oncology. Researchers have explored its potential in treating infectious diseases by targeting bacterial enzymes essential for pathogen survival. For instance, studies have indicated that derivatives of this compound can inhibit bacterial DNA gyrase and topoisomerase IV, which are vital for bacterial replication. This dual functionality makes it an attractive candidate for developing broad-spectrum antibiotics capable of combating drug-resistant strains.

In conclusion,< strong>CAS No: 1202179-41-6, corresponding to7-bromo-2-ethyl-imidazo[1,2-a]pyridine, is a multifaceted compound with significant implications in pharmaceutical research. Its unique structural features enable diverse functionalization strategies, making it a valuable scaffold for drug discovery. Whether targeting neurological disorders or infectious diseases,< strong>this imidazopyridine derivative offers promising avenues for therapeutic intervention. As computational methods continue to refine our understanding of its pharmacological properties,< strong>CAS No: 1202179-41-6's role in advancing medicinal chemistry is poised to expand further.

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