7-苯胺基香豆素-4-乙酸 | 82412-15-5

• 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
• 中文名称: 7-苯胺基香豆素-4-乙酸
• 英文名称: (7-anilino-2-oxo-2H-chromen-4-yl)acetic acid
• 英文别名: 7-anilinocoumarin-4-acetic acid；7-Anilino-4-carboxymethyl-cumarin；2-(7-anilino-2-oxochromen-4-yl)acetic acid
• CAS: 82412-15-5
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: CSPJQOJRUAXBGR-UHFFFAOYSA-N

物化性质

• 最大波长(λmax)：
  262 nm, 375 nm (H2O); 269 nm, 376 nm (EtOH); 272 nm, 378 nm (Cyclohexane)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-苯胺基香豆素-4-乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[2-(3-benzoxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl]-2-(7-anilino-2-oxo-2H-chromen-4-yl)acetamide
  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：

  1,3-丙酮二羧酸二乙酯 在 sodium hydroxide 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 生成 7-苯胺基香豆素-4-乙酸
  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

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• New Fluorescence probes for drug-albumin intereaction studies.
  作者：SHUJIRO GOYA、AKIRA TAKADATE、HIROYUKI FUJINO、MASAKI OTAGIRI、KANETO UEKAMA

  DOI：10.1248/cpb.30.1363

  日期：——

  Some new and known coumarincarboxylic acids were synthesized for use as fluorescence probes. The fluorescence properties of these compounds were examined in various solvents and albumin solutions. The fluorescence of 7-anilinocoumarin-4-acetic acid (I) was significantly enhanced in nonpolar solvents and in the presence of human serum albumin (HSA). The binding parameters of I were estimated from the fluorescence enhancement and spectral change of I bound to HSA. The Scatchard plots and the continuous variation plots indicated that only the primary site was capable of enhancing the fluorescence and causing the spectral changes of I. Digitoxin displaced I from its primary site on HSA, but site 1 and site 2 drugs on the basis of Sudlow's classification did not significantly displace the probe. The present data indicate that I may be useful as a third site marker.

  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。
• Use of oligonucleotides for inhibition of complement activation
  申请人：——

  公开号：US20020082227A1

  公开（公告）日：2002-06-27

  Methods for inhibiting complement activation using antisense oligonucleotides, preferably modified oligonucleotides. These compounds may be used therapeutically to treat undesirable complement-mediated events such as inflammation.

  使用反义寡核苷酸，最好是改良的寡核苷酸，来抑制补体激活的方法。这些化合物可用于治疗不良的补体介导事件，如炎症。
• Inhibition of complement activation and complement modulation by use of modified oligonucleotides
  申请人：——

  公开号：US20040038925A1

  公开（公告）日：2004-02-26

  Methods for inhibiting complement activation using antisense oligonucleotides, preferably modified oligonucleotides. These compounds may be used therapeutically to treat undesirable complement-mediated events such as inflammation.

  使用反义寡核苷酸，优选修饰寡核苷酸，抑制补体激活的方法。这些化合物可用于治疗不良的补体介导事件，如炎症。
• LIGAND-CONJUGATED OLIGOMERIC COMPOUNDS
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1185305A1

  公开（公告）日：2002-03-13