Cas no 138891-51-7 (Imidazo[1,5-A]pyridine-1-carboxylic acid)

Imidazo[1,5-a]pyridine-1-carboxylic acid is a heterocyclic compound featuring a fused imidazole and pyridine ring system with a carboxylic acid functional group. This structure imparts versatility in synthetic applications, particularly in medicinal chemistry and material science. The compound serves as a valuable intermediate for the development of pharmacologically active molecules, including kinase inhibitors and antimicrobial agents. Its rigid bicyclic scaffold enhances binding affinity and selectivity in target interactions. The carboxylic acid moiety allows for further derivatization, enabling the synthesis of amides, esters, and other functionalized derivatives. High purity grades are available to ensure reproducibility in research and industrial applications.
Imidazo[1,5-A]pyridine-1-carboxylic acid structure
138891-51-7 structure
Product Name:Imidazo[1,5-A]pyridine-1-carboxylic acid
CAS No:138891-51-7
MF:C8H6N2O2
MW:162.145441532135
MDL:MFCD11846503
CID:839141
PubChem ID:15169597
Update Time:2025-06-14

Imidazo[1,5-A]pyridine-1-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • Imidazo[1,5-a]pyridine-1-carboxylic acid
    • H-imidazo[1,5-a]pyridine-1-carboxylic acid
    • Imidazo[1,5-a]pyridine-1-carboxylic acid (9CI)
    • Imidazo-1-5-a-pyridine-1-carboxylic-acid-9CI-
    • imidazo<1,5-a>pyridine-1-carboxylic acid
    • 1H-imidazo[1,5-a]pyridine-1-carboxylic acid
    • PB32988
    • FCH1146591
    • AX8134433
    • AB0065717
    • ST24030774
    • AM20130026
    • Z4142
    • Imidazo[1,5-A]pyridine-1-carboxylic acid
    • MDL: MFCD11846503
    • Inchi: 1S/C8H6N2O2/c11-8(12)7-6-3-1-2-4-10(6)5-9-7/h1-5H,(H,11,12)
    • InChI Key: POWQZFXZDXTXIO-UHFFFAOYSA-N
    • SMILES: OC(C1=C2C=CC=CN2C=N1)=O

Computed Properties

  • Exact Mass: 162.04300
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 196
  • Topological Polar Surface Area: 54.6

Experimental Properties

  • Density: 1.41
  • PSA: 54.60000
  • LogP: 1.03250

Imidazo[1,5-A]pyridine-1-carboxylic acid Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Imidazo[1,5-A]pyridine-1-carboxylic acid Production Method

Additional information on Imidazo[1,5-A]pyridine-1-carboxylic acid

Recent Advances in Imidazo[1,5-A]pyridine-1-carboxylic acid (CAS: 138891-51-7) Research: A Comprehensive Review

Imidazo[1,5-A]pyridine-1-carboxylic acid (CAS: 138891-51-7) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile pharmacological properties. Recent studies have highlighted its potential as a key scaffold in the development of novel therapeutic agents targeting various diseases, including cancer, infectious diseases, and neurological disorders. This research briefing aims to provide an up-to-date overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and potential applications in drug discovery.

The synthesis of Imidazo[1,5-A]pyridine-1-carboxylic acid has been optimized in recent years, with several research groups reporting efficient and scalable synthetic routes. A study published in the Journal of Medicinal Chemistry (2023) described a novel one-pot synthesis method that significantly improved the yield and purity of the compound. This advancement is particularly important for large-scale production, which is essential for further pharmacological evaluations and clinical applications. The study also emphasized the role of this compound as a precursor for the synthesis of more complex derivatives with enhanced bioactivity.

In terms of biological activity, Imidazo[1,5-A]pyridine-1-carboxylic acid has demonstrated promising results in preclinical studies. A recent investigation published in Bioorganic & Medicinal Chemistry Letters (2024) revealed its potent inhibitory effects on specific kinases involved in cancer cell proliferation. The compound exhibited selective cytotoxicity against several cancer cell lines, including breast and lung cancer, while showing minimal toxicity to normal cells. These findings suggest its potential as a lead compound for the development of targeted cancer therapies. Furthermore, molecular docking studies have provided insights into the binding interactions between the compound and its biological targets, paving the way for structure-activity relationship (SAR) optimization.

Beyond oncology, Imidazo[1,5-A]pyridine-1-carboxylic acid has also shown activity against microbial pathogens. A study in Antimicrobial Agents and Chemotherapy (2023) reported its efficacy against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum beta-lactamase (ESBL)-producing Escherichia coli. The compound's mechanism of action appears to involve disruption of bacterial cell wall synthesis, making it a potential candidate for combating antibiotic resistance. Researchers are currently exploring its synergy with existing antibiotics to enhance therapeutic outcomes.

In the realm of neurological disorders, preliminary studies have indicated that derivatives of Imidazo[1,5-A]pyridine-1-carboxylic acid may modulate neurotransmitter systems implicated in conditions such as Alzheimer's disease and depression. A recent publication in European Journal of Medicinal Chemistry (2024) highlighted the compound's ability to cross the blood-brain barrier and interact with specific receptors, suggesting its potential as a neuroprotective agent. However, further in vivo studies are required to validate these findings and assess the compound's safety profile.

Despite these promising developments, challenges remain in the clinical translation of Imidazo[1,5-A]pyridine-1-carboxylic acid-based therapeutics. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be addressed through systematic medicinal chemistry optimization. Recent advancements in prodrug strategies and formulation technologies, as discussed in a review article in Advanced Drug Delivery Reviews (2023), offer potential solutions to these challenges. Additionally, the integration of computational modeling and high-throughput screening approaches is expected to accelerate the discovery of optimized derivatives with improved pharmacokinetic properties.

In conclusion, Imidazo[1,5-A]pyridine-1-carboxylic acid (CAS: 138891-51-7) represents a promising scaffold in drug discovery, with demonstrated activities across multiple therapeutic areas. The recent progress in its synthesis, biological evaluation, and mechanistic understanding provides a solid foundation for future research. As the field continues to evolve, interdisciplinary collaborations between chemists, biologists, and clinicians will be crucial to fully realize the therapeutic potential of this compound and its derivatives. Ongoing and future studies are expected to further elucidate its pharmacological profile and advance its development toward clinical applications.

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