Cas no 1332589-39-5 (Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide)

Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide is a brominated imidazopyridine derivative with significant utility in pharmaceutical and agrochemical research. The compound serves as a versatile intermediate in the synthesis of bioactive molecules, particularly those targeting heterocyclic scaffolds. Its hydrobromide salt form enhances stability and solubility, facilitating handling in synthetic applications. The presence of both bromine and ester functional groups allows for further derivatization, making it valuable for structure-activity relationship (SAR) studies. This compound is particularly relevant in the development of kinase inhibitors and antimicrobial agents. Its well-defined crystalline structure ensures consistent purity, supporting reproducible results in experimental workflows.
Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide structure
1332589-39-5 structure
Product Name:Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide
CAS No:1332589-39-5
MF:C10H10Br2N2O2
MW:350.006600856781
CID:1028586
PubChem ID:57360970
Update Time:2025-05-21

Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide Chemical and Physical Properties

Names and Identifiers

    • Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide
    • ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate;hydrobromide
    • Imidazo[1,2-a]pyridine-2-carboxylic acid, 5-bromo-, ethyl ester, hydrobromide (1:1)
    • G10353
    • Ethyl5-bromoimidazo[1,2-a]pyridine-2-carboxylatehydrobromide
    • DB-368603
    • 5-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester HBr
    • DTXSID00724370
    • 5-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester hydrobromide
    • 1332589-39-5
    • 5-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester HBr
    • Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate--hydrogen bromide (1/1)
    • BS-20908
    • Inchi: 1S/C10H9BrN2O2.BrH/c1-2-15-10(14)7-6-13-8(11)4-3-5-9(13)12-7;/h3-6H,2H2,1H3;1H
    • InChI Key: DPBZWALWXQGKPB-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2=NC(C(=O)OCC)=CN21.Br

Computed Properties

  • Exact Mass: 349.90885g/mol
  • Monoisotopic Mass: 347.91090g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 250
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 43.6?2

Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide Pricemore >>

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Additional information on Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide

Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide: A Comprehensive Overview

Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide (CAS No. 1332589-39-5) is a highly specialized organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmacology. This compound belongs to the class of imidazo[1,2-a]pyridines, which are known for their unique structural features and diverse biological activities. The presence of a bromine atom at the 5-position of the imidazo[1,2-a]pyridine ring introduces additional complexity and functionality to the molecule, making it a valuable candidate for various applications in drug discovery and development.

The synthesis of Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide involves a series of well-defined chemical reactions. The starting material is typically an imidazole derivative, which undergoes bromination to introduce the bromine atom at the desired position. Subsequent steps involve esterification and hydrobromination to yield the final product. Recent advancements in synthetic methodologies have enabled researchers to optimize the reaction conditions, thereby improving the yield and purity of the compound. These improvements are critical for ensuring the reliability and reproducibility of experimental results in downstream applications.

One of the most intriguing aspects of Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide is its pharmacological activity. Studies have demonstrated that this compound exhibits potent inhibitory effects on several key enzymes and receptors involved in various disease pathways. For instance, it has been shown to inhibit kinases associated with cancer cell proliferation and survival. Additionally, its ability to modulate ion channels makes it a promising candidate for treating neurological disorders such as epilepsy and chronic pain. Recent research has further elucidated its mechanism of action, revealing that it interacts with specific binding sites on target proteins, leading to allosteric modulation or competitive inhibition.

The structural versatility of Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide also lends itself to applications in materials science. Its aromatic system and functional groups make it suitable for use as a building block in constructing advanced materials such as organic semiconductors and sensors. For example, derivatives of this compound have been incorporated into thin-film transistors (TFTs) to enhance their electronic properties. The bromine atom plays a crucial role in modulating the electronic characteristics of the material, enabling better charge transport and device performance.

In terms of therapeutic potential, Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide has shown promise in preclinical models of inflammation and oxidative stress. Its ability to scavenge reactive oxygen species (ROS) and inhibit pro-inflammatory cytokines suggests that it could be developed into an anti-inflammatory agent for treating conditions such as arthritis and cardiovascular diseases. Recent studies have also explored its potential as a radiosensitizer in cancer therapy, where it enhances the efficacy of radiation treatment by increasing DNA damage in tumor cells while sparing normal tissues.

Despite its numerous advantages, Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide faces challenges related to its pharmacokinetic properties. Initial studies indicate that it has limited bioavailability due to rapid metabolism and poor solubility in physiological fluids. To address these issues, researchers are investigating various strategies such as prodrug design and nanotechnology-based delivery systems. For instance, encapsulating the compound in lipid nanoparticles has significantly improved its stability and uptake in target tissues.

In conclusion, Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide is a multifaceted compound with immense potential across multiple scientific domains. Its unique structure enables diverse biological activities and material properties, making it a valuable asset for both academic research and industrial applications. As ongoing studies continue to uncover new insights into its mechanisms and applications, this compound is poised to play a pivotal role in advancing our understanding of complex biological systems and developing innovative therapeutic interventions.

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