Cas no 353258-33-0 (6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid)

6,8-Dichloroimidazo[1,2-a]pyridine-2-carboxylic acid is a heterocyclic compound featuring a fused imidazo[1,2-a]pyridine core with chloro substituents at the 6 and 8 positions and a carboxylic acid group at the 2-position. This structure imparts reactivity suitable for further functionalization, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The dichloro substitution enhances electrophilic properties, facilitating cross-coupling and nucleophilic substitution reactions. The carboxylic acid moiety allows for derivatization into esters, amides, or other derivatives. Its rigid heterocyclic framework contributes to stability while enabling applications in medicinal chemistry, particularly in the development of bioactive molecules. The compound is typically handled under controlled conditions due to its reactive functional groups.
6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid structure
353258-33-0 structure
Product Name:6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid
CAS No:353258-33-0
MF:C8H4Cl2N2O2
MW:231.035559654236
MDL:MFCD01833014
CID:3111703
PubChem ID:4683562
Update Time:2025-08-03

6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid Chemical and Physical Properties

Names and Identifiers

    • 6,8-dichloroimidazo[1,2-a]pyridine-2-carboxylic acid
    • DPA25833
    • 6,8-dichloroimidazo[1,2-a]pyridine-2-carboxylicacid
    • 353258-33-0
    • EN300-198988
    • 878-182-3
    • 6,8-Dichloroimidazo(1,2-a)pyridine-2-carboxylic acid
    • AI-204/31692054
    • Oprea1_603540
    • AKOS017547959
    • G53277
    • Z1269165982
    • 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid
    • MDL: MFCD01833014
    • Inchi: 1S/C8H4Cl2N2O2/c9-4-1-5(10)7-11-6(8(13)14)3-12(7)2-4/h1-3H,(H,13,14)
    • InChI Key: OKRIIMVNXKTCPK-UHFFFAOYSA-N
    • SMILES: ClC1=CC(=CN2C=C(C(=O)O)N=C21)Cl

Computed Properties

  • Exact Mass: 229.9649828Da
  • Monoisotopic Mass: 229.9649828Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 251
  • 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: 2.9
  • Topological Polar Surface Area: 54.6?2

6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid Pricemore >>

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Additional information on 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid

Introduction to 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid (CAS No. 353258-33-0)

6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid, identified by the Chemical Abstracts Service Number (CAS No.) 353258-33-0, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the imidazopyridine class, a structural motif known for its broad biological activity and utility in drug discovery. The presence of two chlorine atoms at the 6th and 8th positions enhances its reactivity and makes it a valuable scaffold for further chemical modifications.

The structural framework of 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid consists of an imidazole ring fused with a pyridine ring, with the carboxylic acid functional group at the 2-position and chlorine substituents at the 6th and 8th positions. This specific arrangement contributes to its unique electronic properties and interaction potential with biological targets. The compound's dual chlorination not only influences its electronic distribution but also provides multiple sites for chemical manipulation, enabling the synthesis of derivatives with tailored pharmacological profiles.

In recent years, there has been a surge in research focused on developing novel heterocyclic compounds for therapeutic applications. Imidazopyridines, in particular, have emerged as a promising class of molecules due to their ability to modulate various biological pathways. 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid has been explored as a key intermediate in the synthesis of more complex molecules designed to interact with biological receptors and enzymes. Its role in drug discovery has been highlighted in several studies aimed at identifying compounds with potential antimicrobial, anticancer, and anti-inflammatory properties.

One of the most compelling aspects of 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid is its versatility as a building block. The carboxylic acid group at the 2-position allows for further functionalization through esterification, amidation, or coupling reactions, enabling the creation of diverse derivatives. These derivatives can then be screened for biological activity across a range of targets. For instance, researchers have utilized this compound to develop inhibitors targeting enzymes involved in cancer metabolism and pathogens resistant to conventional antibiotics.

The pharmaceutical industry has been particularly interested in imidazopyridines due to their favorable pharmacokinetic properties and low toxicity profiles. 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid has been incorporated into several drug candidates that are currently undergoing preclinical or clinical evaluation. These candidates have shown promise in treating conditions such as chronic infections and solid tumors. The compound's ability to modulate key signaling pathways has made it a valuable asset in the development of next-generation therapeutics.

From a synthetic chemistry perspective, 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid serves as an excellent starting material for exploring new synthetic methodologies. The chlorine atoms at the 6th and 8th positions facilitate cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, allowing for the introduction of aryl or amino groups. Additionally, palladium-catalyzed reactions can be employed to achieve regioselective transformations at these positions. These synthetic strategies have enabled chemists to generate libraries of imidazopyridine derivatives efficiently.

The biological activity of 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid has been investigated across multiple therapeutic areas. Studies have demonstrated its potential as an antiviral agent by interfering with viral replication mechanisms. Furthermore, its interaction with bacterial enzymes has been explored as a means to develop novel antibiotics targeting resistant strains. In oncology research, this compound has been shown to inhibit kinases involved in tumor growth and angiogenesis.

The development of high-throughput screening (HTS) platforms has accelerated the discovery process for compounds like 6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid. These platforms allow researchers to rapidly assess thousands of compounds for activity against various biological targets. The ease with which this compound can be synthesized and modified makes it an ideal candidate for HTS campaigns aimed at identifying lead compounds for drug development.

In conclusion,6,8-Dichloroimidazo1,2-apyridine-2-carboxylic Acid (CAS No. 353258-33-0) represents a significant advancement in pharmaceutical chemistry due to its structural versatility and broad biological activity. Its role as an intermediate in synthesizing novel drug candidates underscores its importance in medicinal research. As advancements continue in synthetic methodologies and high-throughput screening technologies,imidazopyridines like this will remain at the forefront of drug discovery efforts aimed at addressing unmet medical needs.

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