Cas no 26474-95-3 (5-Chloro-3-hydroxybenzofuran-2-carboxamide)

5-Chloro-3-hydroxybenzofuran-2-carboxamide is a heterocyclic compound featuring a benzofuran core substituted with chloro, hydroxy, and carboxamide functional groups. Its structural framework makes it a valuable intermediate in pharmaceutical and agrochemical research, particularly in the synthesis of bioactive molecules. The presence of both electron-withdrawing (chloro) and electron-donating (hydroxy) groups enhances its reactivity and potential for further derivatization. The carboxamide moiety contributes to its stability and compatibility with various synthetic pathways. This compound is of interest in medicinal chemistry due to its potential applications in developing enzyme inhibitors or receptor modulators. Its well-defined purity and consistent performance make it suitable for rigorous laboratory and industrial use.
5-Chloro-3-hydroxybenzofuran-2-carboxamide structure
26474-95-3 structure
Product Name:5-Chloro-3-hydroxybenzofuran-2-carboxamide
CAS No:26474-95-3
MF:C9H6ClNO3
MW:211.601841449738
CID:1092493
PubChem ID:54718765
Update Time:2025-05-21

5-Chloro-3-hydroxybenzofuran-2-carboxamide Chemical and Physical Properties

Names and Identifiers

    • 5-Chloro-3-hydroxybenzofuran-2-carboxamide
    • 5-chloro-3-hydroxy-1-benzofuran-2-carboxamide
    • SCHEMBL11126153
    • A919521
    • 26474-95-3
    • 2-Benzofurancarboxamide, 5-chloro-3-hydroxy-
    • Inchi: 1S/C9H6ClNO3/c10-4-1-2-6-5(3-4)7(12)8(14-6)9(11)13/h1-3,12H,(H2,11,13)
    • InChI Key: MFYLUJPNKQUTST-UHFFFAOYSA-N
    • SMILES: ClC1C=CC2=C(C=1)C(=C(C(N)=O)O2)O

Computed Properties

  • Exact Mass: 211.0036207g/mol
  • Monoisotopic Mass: 211.0036207g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 248
  • 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: 2.4
  • Topological Polar Surface Area: 76.5?2

5-Chloro-3-hydroxybenzofuran-2-carboxamide Security Information

  • Storage Condition:Sealed in dry,2-8°C

5-Chloro-3-hydroxybenzofuran-2-carboxamide Pricemore >>

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Additional information on 5-Chloro-3-hydroxybenzofuran-2-carboxamide

Research Brief on 5-Chloro-3-hydroxybenzofuran-2-carboxamide (CAS: 26474-95-3): Recent Advances and Applications

5-Chloro-3-hydroxybenzofuran-2-carboxamide (CAS: 26474-95-3) is a chemical compound of significant interest in the field of chemical biology and pharmaceutical research. Recent studies have explored its potential as a versatile scaffold for drug development, particularly in the context of antimicrobial, anticancer, and anti-inflammatory applications. This research brief synthesizes the latest findings on this compound, highlighting its molecular mechanisms, synthetic pathways, and therapeutic potential.

A 2023 study published in the Journal of Medicinal Chemistry investigated the antimicrobial properties of 5-Chloro-3-hydroxybenzofuran-2-carboxamide derivatives. The research team synthesized a series of analogs and evaluated their efficacy against multidrug-resistant bacterial strains, including Staphylococcus aureus and Escherichia coli. The results demonstrated that specific derivatives exhibited potent antibacterial activity, with minimum inhibitory concentrations (MICs) comparable to existing antibiotics. The study also identified the compound's ability to disrupt bacterial cell wall synthesis as a key mechanism of action.

In the realm of oncology, a recent preprint on bioRxiv (2024) explored the anticancer potential of 5-Chloro-3-hydroxybenzofuran-2-carboxamide in glioblastoma models. The compound was found to inhibit the proliferation of glioblastoma cells by targeting the PI3K/AKT/mTOR signaling pathway, a critical regulator of cancer cell survival and growth. Notably, the study reported synergistic effects when the compound was combined with temozolomide, a standard chemotherapy agent, suggesting its potential as an adjunct therapy for glioblastoma.

From a synthetic chemistry perspective, advancements have been made in optimizing the production of 5-Chloro-3-hydroxybenzofuran-2-carboxamide. A 2023 paper in Organic Process Research & Development described a novel, scalable synthesis route that improves yield and reduces environmental impact. The new method employs green chemistry principles, such as solvent-free reactions and catalytic processes, making it more sustainable for industrial-scale production.

Despite these promising developments, challenges remain in the clinical translation of 5-Chloro-3-hydroxybenzofuran-2-carboxamide-based therapeutics. Pharmacokinetic studies indicate that the compound exhibits moderate bioavailability, prompting ongoing research into prodrug strategies and formulation optimizations. Additionally, further toxicological evaluations are needed to ensure safety profiles meet regulatory standards for human use.

In conclusion, 5-Chloro-3-hydroxybenzofuran-2-carboxamide (CAS: 26474-95-3) represents a compelling case study in modern drug discovery, showcasing how structural optimization and mechanistic understanding can unlock therapeutic potential. The compound's diverse biological activities and recent synthetic advancements position it as a valuable candidate for future pharmaceutical development, particularly in addressing unmet medical needs in infectious diseases and oncology.

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