Basic Information: 6,7-Dimethoxy-4-(4-nitrophenoxy)quinoline (also known as Cabozantinib Nitro Analog or Cabozantinib Impurity 2) is a synthetic quinoline derivative with the molecular formula C₁₇H₁₄N₂O₅ and a molecular weight of approximately 326.30 g/mol. 6,7-Dimethoxy-4-(4-nitrophenoxy)quinoline is a related compound of Cabozantinib with potential anticancer activity. It can be used in the preparation of nicotinamide derivatives as Aurora kinase inhibitors, nquinolinyloxyphenylbenzenesulfonamides as AXL kinase inhibitors, N-phenyl-N'-{4-(4-quinolyloxy)phenyl}ureas as vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase inhibitors, and phenoxyquinolines as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase.
Relationship to Cabozantinib: The compound is a nitro-substituted analog of Cabozantinib, a U.S. FDA-approved multikinase inhibitor for the treatment of medullary thyroid cancer and advanced renal cell carcinoma. Cabozantinib exerts its therapeutic effect by inhibiting, among others, the tyrosine kinase c-Met. CAS:190728-24-6 is widely recognized in pharmaceutical research and quality control as Cabozantinib Impurity 2 or Cabozantinib Nitro Analog. It serves as a critical reference standard for impurity profiling of Cabozantinib active pharmaceutical ingredient (API).
Applications in Scientific Research: The compound has significant utility across multiple research domains, primarily by virtue of its structural relationship to clinically approved cabozantinib and its pharmacologically active 4-phenoxyquinoline scaffold. Key applications include: --Cancer Research and Drug Discovery This quinoline derivative is a lead compound for the development of new anticancer therapies and serves as a key intermediate in the preparation of Cabozantinib and related analogs. It is used in the preparation of nicotinamide derivatives acting as Aurora kinase inhibitors. Aurora kinases are critical regulators of mitosis and represent validated targets for cancer therapy. --Angiogenesis Research The compound facilitates the preparation of N-phenyl-N’-{4-(4-quinolyloxy)phenyl}ureas as VEGFR-2 tyrosine kinase inhibitors, which may lead to new treatments for diseases characterized by excessive angiogenesis. Angiogenesis is a key hallmark of tumor growth and metastasis. Beyond VEGFR-2 inhibition, the 4-phenoxyquinoline core of this compound also allows for the preparation of AXL kinase inhibitors (used in preparation of quinolinyloxyphenylbenzenesulfonamides) and PDGFR tyrosine kinase inhibitors (used in preparation of phenoxyquinolines as specific inhibitors of platelet-derived growth factor receptor). --Pharmaceutical Quality Control As a well-characterized impurity reference standard, CAS 190728-24-6 is employed in quality control workflows and impurity profiling of Cabozantinib API during commercial production, with detailed characterization data compliant with regulatory guidelines.. --Third-Generation Photovoltaics Quinoline derivatives, including this compound, have gained attention in third-generation photovoltaic applications, leveraging their favorable electronic properties. Conclusion: CAS 190728-24-6 (6,7-Dimethoxy-4-(4-nitrophenoxy)quinoline) is a synthetically accessible quinoline derivative with well-defined chemical properties. It serves multiple critical roles in pharmaceutical research: as a key impurity reference standard for Cabozantinib quality control, as a chemical intermediate for kinase inhibitor development, and as a valuable tool compound in cancer and angiogenesis research. Its continued availability from multiple global suppliers supports ongoing drug development and analytical quality assurance efforts. Product manager: Joy Wu CONTACT/Email address: Joy@coreychem.com
