ethyl 7-anilinocoumarin-4-acetate | 82412-18-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ethyl 7-anilinocoumarin-4-acetate
• 英文别名: ethyl (7-anilino-2-oxo-2H-chromen-4-yl)acetate；4-Aethoxycarbonylmethyl-7-anilino-cumarin；(7-anilino-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester；ethyl 2-(7-anilino-2-oxochromen-4-yl)acetate
• CAS: 82412-18-8
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: KHISCLICOVSONG-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  501.3±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 7-anilinocoumarin-4-acetate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 7-Anilino-4-[2-oxo-2-(2-sulfanylidene-1,3-thiazolidin-3-yl)ethyl]chromen-2-one
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s
• 作为产物：
  描述：

  ethyl acetonedicarboxylate 、 间羟基二苯胺 在 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 ethyl 7-anilinocoumarin-4-acetate
  参考文献：
  名称：

  New Fluorescence probes for drug-albumin intereaction studies.

  摘要：

  一些新的和已知的香豆酸类化合物被合成为荧光探针。这些化合物的荧光特性在各种溶剂和白蛋白溶液中进行了研究。7-氨基香豆酸-4-乙酸（I）在非极性溶剂和人血清白蛋白（HSA）存在下的荧光显著增强。根据I与HSA结合时的荧光增强和光谱变化估计了I的结合参数。Scatchard图和连续变化图表明，只有主要位点能够增强荧光并导致I的光谱变化。地高辛将I从HSA的主要位点中置换出来，但根据Sudlow分类，位点1和位点2的药物并未显著置换该探针。目前的数据表明，I可能作为第三位点标记物有一定的应用潜力。

  DOI：

  10.1248/cpb.30.1363