Cas no 49850-62-6 (1,5-naphthyridine-2-carboxylic acid)

1,5-Naphthyridine-2-carboxylic acid is a heterocyclic carboxylic acid derivative with a naphthyridine core structure, offering versatility as a building block in organic synthesis and pharmaceutical applications. Its rigid bicyclic framework and carboxylic acid functional group make it a valuable intermediate for constructing complex molecules, particularly in medicinal chemistry for drug discovery. The compound's electron-deficient aromatic system enables participation in various coupling reactions, while the carboxyl group allows for further derivatization via amidation or esterification. Its structural features contribute to potential biological activity, making it useful in developing kinase inhibitors or other therapeutic agents. The compound exhibits good thermal stability and is typically handled under standard laboratory conditions.
1,5-naphthyridine-2-carboxylic acid structure
49850-62-6 structure
Product Name:1,5-naphthyridine-2-carboxylic acid
CAS No:49850-62-6
MF:C9H6N2O2
MW:174.156141757965
MDL:MFCD06801138
CID:830012
PubChem ID:12426408
Update Time:2025-06-08

1,5-naphthyridine-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 1,5-naphthyridine-2-carboxylic acid
    • [1,5]naphthylidine-2-carboxylic acid
    • [1,5]naphthyridine-2-carboxylic acid
    • 1,5-Naphthyridin-2-carbonsaeure
    • 1,8-Naphthyridin-2-butyricacid
    • [1,5]Naphthyridine-2-carboxylic acid, AldrichCPR
    • DA-30169
    • XCFUFRWRMISKRZ-UHFFFAOYSA-N
    • F1957-0374
    • ZBA85062
    • 1,5-NAPHTHYRIDINE-2-CARBOXYLICACID
    • PB30868
    • AKOS006344718
    • DTXSID60497750
    • MFCD06801138
    • SCHEMBL841536
    • 49850-62-6
    • SY013850
    • EN300-332150
    • CS-0006527
    • PS-3285
    • P10420
    • MDL: MFCD06801138
    • Inchi: 1S/C9H6N2O2/c12-9(13)8-4-3-6-7(11-8)2-1-5-10-6/h1-5H,(H,12,13)
    • InChI Key: XCFUFRWRMISKRZ-UHFFFAOYSA-N
    • SMILES: OC(C1=CC=C2C(C=CC=N2)=N1)=O

Computed Properties

  • Exact Mass: 174.04300
  • Monoisotopic Mass: 174.042927438g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 208
  • 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: 1.1
  • Topological Polar Surface Area: 63.1?2

Experimental Properties

  • Density: 1.421
  • Melting Point: >200°C
  • Boiling Point: 366.8°C at 760 mmHg
  • Flash Point: 175.6°C
  • Refractive Index: 1.697
  • PSA: 63.08000
  • LogP: 1.32800

1,5-naphthyridine-2-carboxylic acid Security Information

1,5-naphthyridine-2-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%

1,5-naphthyridine-2-carboxylic acid Pricemore >>

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Additional information on 1,5-naphthyridine-2-carboxylic acid

Recent Advances in the Study of 1,5-Naphthyridine-2-carboxylic Acid (CAS: 49850-62-6) in Chemical Biology and Pharmaceutical Research

1,5-Naphthyridine-2-carboxylic acid (CAS: 49850-62-6) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and drug discovery. This compound serves as a key scaffold for the development of novel therapeutic agents, particularly in the areas of oncology, infectious diseases, and inflammation. Recent studies have highlighted its potential as a pharmacophore in the design of kinase inhibitors, antimicrobial agents, and anti-inflammatory drugs. The unique structural features of 1,5-naphthyridine-2-carboxylic acid, including its ability to form hydrogen bonds and participate in π-π stacking interactions, make it an attractive candidate for targeting a wide range of biological macromolecules.

One of the most notable advancements in the study of 1,5-naphthyridine-2-carboxylic acid is its role in the development of kinase inhibitors. Kinases are critical regulators of cellular signaling pathways, and their dysregulation is often associated with cancer and other diseases. Recent research has demonstrated that derivatives of 1,5-naphthyridine-2-carboxylic acid exhibit potent inhibitory activity against various kinases, including EGFR, VEGFR, and CDK4/6. For instance, a study published in the Journal of Medicinal Chemistry (2023) reported the synthesis of a series of 1,5-naphthyridine-2-carboxylic acid derivatives that showed nanomolar potency against EGFR mutants resistant to first-generation inhibitors. These findings underscore the potential of this scaffold in overcoming drug resistance in cancer therapy.

In addition to its applications in oncology, 1,5-naphthyridine-2-carboxylic acid has also been explored as a building block for antimicrobial agents. The rise of multidrug-resistant pathogens has necessitated the discovery of new antibiotics with novel mechanisms of action. A recent study in Bioorganic & Medicinal Chemistry Letters (2023) described the synthesis of 1,5-naphthyridine-2-carboxylic acid derivatives with broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria. These compounds were found to inhibit bacterial DNA gyrase, a validated target for antibiotic development. The study also highlighted the favorable pharmacokinetic properties of these derivatives, suggesting their potential for further development as clinical candidates.

Another area of interest is the anti-inflammatory potential of 1,5-naphthyridine-2-carboxylic acid derivatives. Chronic inflammation is a hallmark of many diseases, including rheumatoid arthritis and inflammatory bowel disease. A recent publication in European Journal of Medicinal Chemistry (2023) reported the design and synthesis of novel 1,5-naphthyridine-2-carboxylic acid-based compounds that selectively inhibit the NLRP3 inflammasome, a key mediator of inflammatory responses. These compounds demonstrated significant efficacy in preclinical models of inflammation, with minimal off-target effects, highlighting their potential as next-generation anti-inflammatory agents.

The synthetic accessibility of 1,5-naphthyridine-2-carboxylic acid and its derivatives has also been a focus of recent research. Advances in catalytic methods, such as transition metal-catalyzed C-H activation and photoredox catalysis, have enabled the efficient and scalable synthesis of diverse 1,5-naphthyridine-2-carboxylic acid derivatives. A study in Organic Letters (2023) described a novel palladium-catalyzed annulation strategy for the rapid construction of 1,5-naphthyridine-2-carboxylic acid scaffolds with high regioselectivity and yield. These methodological innovations are expected to accelerate the exploration of this chemical space for drug discovery.

In conclusion, 1,5-naphthyridine-2-carboxylic acid (CAS: 49850-62-6) represents a promising scaffold in chemical biology and pharmaceutical research, with demonstrated applications in kinase inhibition, antimicrobial therapy, and anti-inflammatory drug development. The recent advancements in the synthesis and biological evaluation of its derivatives underscore its potential to address unmet medical needs. Future research should focus on optimizing the pharmacokinetic and pharmacodynamic properties of these compounds, as well as exploring their mechanisms of action in greater detail. The continued exploration of 1,5-naphthyridine-2-carboxylic acid and its derivatives is likely to yield novel therapeutic agents with significant clinical impact.

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