Cas no 38922-79-1 (Imidazo1,2-apyridine-2-carbonitrile)

Imidazo[1,2-a]pyridine-2-carbonitrile is a heterocyclic organic compound featuring a fused imidazole and pyridine ring system with a nitrile functional group at the 2-position. This structure confers versatility in pharmaceutical and agrochemical applications, serving as a key intermediate in the synthesis of bioactive molecules. Its electron-deficient pyridine core and reactive nitrile group enable diverse functionalization, facilitating the development of inhibitors, ligands, and fluorescent probes. The compound's stability and synthetic accessibility make it valuable for medicinal chemistry research, particularly in designing kinase inhibitors and antimicrobial agents. Its well-defined reactivity profile allows for precise modifications, supporting structure-activity relationship studies in drug discovery.
Imidazo1,2-apyridine-2-carbonitrile structure
38922-79-1 structure
Product Name:Imidazo1,2-apyridine-2-carbonitrile
CAS No:38922-79-1
MF:C8H5N3
MW:143.145400762558
MDL:MFCD11110249
CID:1026237
PubChem ID:14358160
Update Time:2025-06-08

Imidazo1,2-apyridine-2-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • Imidazo[1,2-a]pyridine-2-carbonitrile
    • 2-CyanoiMidazo<1,2-a>pyridin
    • AGN-PC-0015PX
    • AK-68543
    • Ambcb4035398
    • ANW-66299
    • CTK8C1339
    • AS-63287
    • AKOS006238801
    • DA-33551
    • DTXSID70559313
    • CS-0373297
    • EN300-55214
    • 38922-79-1
    • SCHEMBL14629346
    • MFCD11110249
    • Imidazo1,2-apyridine-2-carbonitrile
    • MDL: MFCD11110249
    • Inchi: 1S/C8H5N3/c9-5-7-6-11-4-2-1-3-8(11)10-7/h1-4,6H
    • InChI Key: RLPRLFSCQQQVAE-UHFFFAOYSA-N
    • SMILES: N12C=CC=CC1=NC(C#N)=C2

Computed Properties

  • Exact Mass: 143.048347172g/mol
  • Monoisotopic Mass: 143.048347172g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 193
  • 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: 1.8
  • Topological Polar Surface Area: 41.1?2

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abcr
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Additional information on Imidazo1,2-apyridine-2-carbonitrile

Recent Advances in the Study of Imidazo[1,2-a]pyridine-2-carbonitrile (CAS: 38922-79-1) and Its Applications in Chemical Biology and Medicine

The compound Imidazo[1,2-a]pyridine-2-carbonitrile (CAS: 38922-79-1) has garnered significant attention in recent years due to its versatile pharmacological properties and potential applications in drug discovery. This heterocyclic scaffold is known for its ability to interact with various biological targets, making it a promising candidate for the development of novel therapeutics. Recent studies have focused on elucidating its mechanism of action, optimizing its synthetic pathways, and exploring its efficacy in treating diverse diseases, including cancer, infectious diseases, and neurological disorders.

One of the key breakthroughs in the study of Imidazo[1,2-a]pyridine-2-carbonitrile is its role as a kinase inhibitor. Kinases are critical enzymes involved in signal transduction pathways, and their dysregulation is often associated with cancer and other proliferative diseases. Researchers have demonstrated that derivatives of this compound exhibit potent inhibitory activity against specific kinases, such as cyclin-dependent kinases (CDKs) and protein kinase B (Akt). These findings have paved the way for the development of targeted therapies with improved selectivity and reduced off-target effects.

In addition to its kinase inhibitory properties, Imidazo[1,2-a]pyridine-2-carbonitrile has shown promise as an antimicrobial agent. Recent in vitro and in vivo studies have revealed its efficacy against a range of bacterial and fungal pathogens, including drug-resistant strains. The compound's ability to disrupt microbial cell membranes and interfere with essential metabolic pathways underscores its potential as a broad-spectrum antimicrobial agent. Further research is underway to optimize its pharmacokinetic properties and enhance its bioavailability.

The synthetic accessibility of Imidazo[1,2-a]pyridine-2-carbonitrile has also been a focal point of recent investigations. Advances in green chemistry and catalytic methods have enabled the development of more efficient and environmentally friendly synthetic routes. For instance, researchers have successfully employed transition metal-catalyzed reactions and microwave-assisted synthesis to produce high yields of the compound with minimal byproducts. These innovations not only reduce the cost of production but also align with the growing demand for sustainable pharmaceutical manufacturing practices.

Despite these promising developments, challenges remain in the clinical translation of Imidazo[1,2-a]pyridine-2-carbonitrile-based therapeutics. Issues such as solubility, metabolic stability, and potential toxicity need to be addressed through rigorous preclinical testing and structural optimization. Collaborative efforts between academia and industry are essential to overcome these hurdles and accelerate the transition from bench to bedside.

In conclusion, Imidazo[1,2-a]pyridine-2-carbonitrile (CAS: 38922-79-1) represents a multifaceted scaffold with immense potential in chemical biology and medicine. Its diverse pharmacological activities, coupled with advances in synthetic methodologies, position it as a valuable tool for drug discovery and development. Future research should focus on expanding its therapeutic applications, improving its drug-like properties, and exploring its synergistic effects with existing treatments. The continued exploration of this compound is expected to yield significant contributions to the field of medicinal chemistry and beyond.

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