Cas no 566198-35-4 (6-(3-Formylphenyl)-nicotinic acid)

6-(3-Formylphenyl)-nicotinic acid structure
566198-35-4 structure
Product Name:6-(3-Formylphenyl)-nicotinic acid
CAS No:566198-35-4
MF:C13H9NO3
MW:227.215463399887
MDL:MFCD18316833
CID:945673
PubChem ID:12028318
Update Time:2025-07-20

6-(3-Formylphenyl)-nicotinic acid Chemical and Physical Properties

Names and Identifiers

    • 6-(3-Formylphenyl)-nicotinic acid
    • 6-(3-formylphenyl)pyridine-3-carboxylic acid
    • SCHEMBL2557229
    • 6-(3-FORMYLPHENYL)NICOTINIC ACID
    • DTXSID70476076
    • DB-317860
    • A1-28729
    • 566198-35-4
    • MFCD18316833
    • NCGC00374173-01
    • MDL: MFCD18316833
    • Inchi: 1S/C13H9NO3/c15-8-9-2-1-3-10(6-9)12-5-4-11(7-14-12)13(16)17/h1-8H,(H,16,17)
    • InChI Key: OVGILAKIAUTIJH-UHFFFAOYSA-N
    • SMILES: OC(C1=CN=C(C=C1)C1C=CC=C(C=O)C=1)=O

Computed Properties

  • Exact Mass: 227.05800
  • Monoisotopic Mass: 227.058243149g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 292
  • 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: 1.5
  • Topological Polar Surface Area: 67.3?2

Experimental Properties

  • PSA: 67.26000
  • LogP: 2.25930

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Additional information on 6-(3-Formylphenyl)-nicotinic acid

Recent Advances in the Application of 6-(3-Formylphenyl)-nicotinic acid (CAS: 566198-35-4) in Chemical Biology and Pharmaceutical Research

The compound 6-(3-Formylphenyl)-nicotinic acid (CAS: 566198-35-4) has recently emerged as a promising scaffold in medicinal chemistry and chemical biology research. This bifunctional molecule, featuring both a nicotinic acid moiety and a formylphenyl group, has demonstrated significant potential in drug discovery and bioconjugation applications. Recent studies have highlighted its utility as a versatile building block for the synthesis of novel bioactive compounds and as a key intermediate in the development of targeted therapies.

Structural analysis reveals that the 3-formylphenyl group at the 6-position of the nicotinic acid ring provides an excellent handle for further chemical modifications through reductive amination or nucleophilic addition reactions. This characteristic has been exploited in several recent studies to create libraries of derivatives with enhanced pharmacological properties. The compound's molecular weight of 227.21 g/mol and its balanced lipophilicity make it particularly suitable for developing drug-like molecules with improved bioavailability.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers utilized 6-(3-Formylphenyl)-nicotinic acid as a core structure to develop novel kinase inhibitors. The team synthesized over 50 derivatives by modifying the formyl group and demonstrated potent inhibitory activity against several cancer-related kinases, with IC50 values in the low micromolar range. Molecular docking studies revealed that the nicotinic acid moiety forms critical hydrogen bonds with the kinase active site, while the phenyl ring contributes to hydrophobic interactions.

Another significant application was reported in ACS Chemical Biology, where the compound served as a linker in PROTAC (Proteolysis Targeting Chimera) development. The formyl group was conjugated to an E3 ligase ligand, while the carboxylic acid was used to attach various target protein binders. This approach yielded several effective PROTAC molecules that demonstrated selective degradation of target proteins in cellular models, showcasing the compound's versatility in modern drug discovery platforms.

The pharmaceutical industry has also shown growing interest in 566198-35-4 for its potential in antibody-drug conjugate (ADC) development. Recent patent applications disclose its use as a linker payload in next-generation ADCs, where its stability in circulation and controlled release properties under intracellular conditions offer advantages over traditional linker systems. Stability studies indicate that the compound maintains integrity in plasma for over 72 hours while efficiently releasing payload in lysosomal conditions.

From a synthetic chemistry perspective, recent advances have improved the production scalability of 6-(3-Formylphenyl)-nicotinic acid. A 2024 publication in Organic Process Research & Development describes an optimized three-step synthesis from commercially available starting materials, achieving an overall yield of 68% with excellent purity (>99%). This development addresses previous challenges in large-scale production and makes the compound more accessible for broader research applications.

Ongoing research is exploring the compound's potential in other areas, including as a fluorescent probe for bioimaging (due to its inherent fluorescence properties) and as a metal-chelating agent in diagnostic applications. Preliminary results suggest that derivatives of 566198-35-4 could serve as dual-purpose agents combining therapeutic and diagnostic functions (theranostics).

In conclusion, 6-(3-Formylphenyl)-nicotinic acid (566198-35-4) represents a multifaceted tool in contemporary chemical biology and pharmaceutical research. Its unique structural features, combined with recent synthetic improvements and diverse applications, position it as a valuable compound for future drug discovery efforts. The growing body of research on this molecule suggests it will continue to play a significant role in the development of novel therapeutic agents and research tools in the coming years.

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