Cas no 1116691-26-9 (3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid)

3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid is a heterocyclic compound featuring a bromo-substituted imidazopyridine core with a carboxylic acid functional group at the 8-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of bioactive molecules. The bromine atom offers a reactive site for further functionalization via cross-coupling reactions, while the carboxylic acid group enables derivatization into esters, amides, or other derivatives. Its rigid fused-ring system contributes to enhanced binding affinity in medicinal chemistry applications. The compound is typically used in research settings for the design of kinase inhibitors, antimicrobial agents, and other therapeutic candidates. Proper handling requires standard laboratory safety protocols due to its potential reactivity.
3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid structure
1116691-26-9 structure
Product Name:3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid
CAS No:1116691-26-9
MF:C8H5BrN2O2
MW:241.041500806808
MDL:MFCD17016090
CID:890376
PubChem ID:57415878
Update Time:2025-10-23

3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid
    • 3-Bromo-imidazo[1,2-a]pyridine-8-carboxylic acid
    • AK122727
    • C-8488
    • KB-235353
    • PB21450
    • 2094AA
    • FCH1352012
    • AX8246905
    • AM20050670
    • EN300-2170765
    • 1116691-26-9
    • AS-33730
    • SY097201
    • CS-0051436
    • 3-bromoimidazo[1,2-a]pyridine-8-carboxylicacid
    • SCHEMBL14836815
    • MFCD17016090
    • AKOS016012377
    • DA-17933
    • DTXSID20725566
    • MDL: MFCD17016090
    • Inchi: 1S/C8H5BrN2O2/c9-6-4-10-7-5(8(12)13)2-1-3-11(6)7/h1-4H,(H,12,13)
    • InChI Key: ZXMYLMDOAKZVIA-UHFFFAOYSA-N
    • SMILES: BrC1=CN=C2C(C(=O)O)=CC=CN21

Computed Properties

  • Exact Mass: 239.95345
  • Monoisotopic Mass: 239.95344g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 224
  • 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: 54.6
  • XLogP3: 2.3

Experimental Properties

  • PSA: 54.6

3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid Pricemore >>

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3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid Related Literature

Additional information on 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid

Introduction to 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid (CAS No. 1116691-26-9)

3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid (CAS No. 1116691-26-9) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of imidazopyridines, which are known for their diverse biological activities and potential therapeutic applications. The unique structure of 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid makes it an attractive candidate for various drug discovery and development projects.

The chemical structure of 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid features a bromine atom at the 3-position of the imidazopyridine ring and a carboxylic acid group at the 8-position. This arrangement imparts specific physicochemical properties that influence its biological activity and pharmacological profile. The presence of the bromine atom can enhance the compound's reactivity and binding affinity to target proteins, while the carboxylic acid group can facilitate solubility and metabolic stability.

Recent studies have highlighted the potential of 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid in various therapeutic areas. One notable application is in the treatment of neurodegenerative diseases, such as Alzheimer's and Parkinson's disease. Research has shown that this compound can modulate specific enzymes and receptors involved in neuroprotection and neuroregeneration. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid exhibits potent inhibitory activity against beta-secretase (BACE1), an enzyme implicated in the pathogenesis of Alzheimer's disease.

In addition to its neuroprotective properties, 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid has also shown promise in cancer research. Preclinical studies have indicated that this compound can selectively target cancer cells by disrupting key signaling pathways involved in cell proliferation and survival. A recent publication in Cancer Research reported that 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid effectively inhibits the growth of human breast cancer cells by downregulating the expression of cyclin D1 and inducing apoptosis.

The pharmacokinetic properties of 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid have been extensively studied to optimize its therapeutic potential. In vitro and in vivo experiments have demonstrated that this compound exhibits favorable absorption, distribution, metabolism, and excretion (ADME) characteristics. Its high oral bioavailability and low toxicity profile make it an attractive candidate for further clinical development.

To further explore the therapeutic applications of 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid, several ongoing clinical trials are evaluating its safety and efficacy in various disease models. These trials aim to provide comprehensive data on the compound's pharmacological effects and potential side effects, paving the way for its eventual use as a novel therapeutic agent.

In conclusion, 3-Bromoimidazo[1,2-a]pyridine-8-carboxylic acid (CAS No. 1116691-26-9) is a promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure and biological activities make it a valuable tool for drug discovery and development. As research continues to uncover new insights into its mechanisms of action and therapeutic potential, it is likely that this compound will play an increasingly important role in advancing medical treatments for various diseases.

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