7-diethylamino-N-{[tri-(2-{N-[(3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}ethyl)]methyl}-2-oxo-2H-chromen-3-carboxamide | 1204006-94-9

• 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: 7-diethylamino-N-{[tri-(2-{N-[(3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}ethyl)]methyl}-2-oxo-2H-chromen-3-carboxamide
• CAS: 1204006-94-9
• 化学式: C₆₉H₇₈N₈O₁₂
• 分子量: 1211.42
• InChiKey: SQZLZZSZOXAMJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  89.0
• 可旋转键数：
  29.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  243.54
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  7-diethylamino-N-{[tri-(2-{N-[(3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}ethyl)]methyl}-2-oxo-2H-chromen-3-carboxamide 在 5%-palladium/activated carbon 、 钯 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 以87%的产率得到7-diethylamino-N-{[tri-(2-{N-[(3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}ethyl)]methyl}-2-oxo-2H-chromen-3-carboxamide
  参考文献：
  名称：

  The selective quantification of iron by hexadentate fluorescent probes

  摘要：

  The synthesis of four hexadentate fluorescent probes is described, where the fluorescent moiety is based on either coumarin or fluorescein and the chelating moiety is based on either 3-hydroxypyridin-4-one or 3-hydroxypyran-4-one. The fluorescence is quenched when the probe chelating moieties bind iron. The probes were found to be selective for iron over other metals such as Cu, Zn, Ni, Mn and Co. The effect of Cu on fluorescence quenching can be eliminated in the presence of N, N, N', N'-tetrakis(2-pyridylmethyl)-ethylenediamine. Competition studies demonstrate that the exchange of iron between pyridinone-based probes and apotransferrin is very slow. The ability to scavenge iron from oligomeric iron(III) citrate complexes demonstrate that the pyridinone probes scavenges iron faster than deferiprone and desferrioxamine. The fluorescence intensity of the fluorescein-based probe is quantitatively related to the iron concentration with the limit of detection being 10(8) M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.052
• 作为产物：
  描述：

  7-diethylamino-N-[tri-(2-carboxyethyl)methyl]-2-oxo-2H-chromen-3-carboxamide 、 2-(aminomethyl)-3-(benzyloxy)-1,6-dimethylpyridin-4(1H)-one 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 7-diethylamino-N-{[tri-(2-{N-[(3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}ethyl)]methyl}-2-oxo-2H-chromen-3-carboxamide
  参考文献：
  名称：

  The selective quantification of iron by hexadentate fluorescent probes

  摘要：

  The synthesis of four hexadentate fluorescent probes is described, where the fluorescent moiety is based on either coumarin or fluorescein and the chelating moiety is based on either 3-hydroxypyridin-4-one or 3-hydroxypyran-4-one. The fluorescence is quenched when the probe chelating moieties bind iron. The probes were found to be selective for iron over other metals such as Cu, Zn, Ni, Mn and Co. The effect of Cu on fluorescence quenching can be eliminated in the presence of N, N, N', N'-tetrakis(2-pyridylmethyl)-ethylenediamine. Competition studies demonstrate that the exchange of iron between pyridinone-based probes and apotransferrin is very slow. The ability to scavenge iron from oligomeric iron(III) citrate complexes demonstrate that the pyridinone probes scavenges iron faster than deferiprone and desferrioxamine. The fluorescence intensity of the fluorescein-based probe is quantitatively related to the iron concentration with the limit of detection being 10(8) M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.052