N-[2-N,N-bis(2-pyridylmethyl)aminomethylquinolin-6-yl]carbamic acid benzyl ester | 784157-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[2-N,N-bis(2-pyridylmethyl)aminomethylquinolin-6-yl]carbamic acid benzyl ester
• CAS: 784157-43-3
• 化学式: C₃₀H₂₇N₅O₂
• 分子量: 489.577
• InChiKey: IQKAADIBMLZHRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.24
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[2-N,N-bis(2-pyridylmethyl)aminomethylquinolin-6-yl]carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-{N-[2-N,N-bis(2-pyridylmethyl)aminomethylquinolin-6-yl]carbamoylmethyl}-N,N',N'',N''-diethylenetriaminetetraacetic acid
  参考文献：
  名称：

  Development of a Zinc Ion-Selective Luminescent Lanthanide Chemosensor for Biological Applications

  摘要：

  Detection of chelatable zinc (Zn2+) in biological studies has attracted much attention recently, because chelatable Zn2+ plays important roles in many biological systems. Lanthanicle complexes (Eu3+, Tb3+, etc.) have excellent spectroscopic properties for biological applications, such as long luminescence lifetimes of the order of milliseconds, a large Stoke's shift of >200 nm, and high water solubility. Herein, we present the design and synthesis of a novel lanthanide sensor molecule, [Eu-7], for detecting Zn2+. This europium (Eu3+) complex employs a quinolyl ligand as both a chromophore and an acceptor for Zn2+. Upon addition of Zn2+ to a solution of [Eu-7], the luminescence of Eu3+ is strongly enhanced, with high selectivity for Zn2+ over other biologically relevant metal cations. One of the important advantages of [Eu-7] is that this complex can be excited with longer excitation wavelengths (around 340 nm) as compared with previously reported Zn2+-sensitive luminescent lamthanide sensors, whose excitation wavelength is at too high an energy level for biological applications. The usefulness of [Eu-7] for monitoring Zn2+ changes in living HeLa cells was confirmed. This novel Zn2+-selective luminescent lanthanide chemosensor [Eu-7] should be an excellent lead compound for the development of a range of novel luminescent lanthanide chemosensors for biological applications.

  DOI：

  10.1021/ja0469333
• 作为产物：
  描述：

  N-(2-methyl-1-oxyquinolin-6-yl)carbamic acid benzyl ester 在 sodium carbonate 、 对甲苯磺酰氯 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 51.0h， 生成 N-[2-N,N-bis(2-pyridylmethyl)aminomethylquinolin-6-yl]carbamic acid benzyl ester
  参考文献：
  名称：

  Development of a Zinc Ion-Selective Luminescent Lanthanide Chemosensor for Biological Applications

  摘要：

  Detection of chelatable zinc (Zn2+) in biological studies has attracted much attention recently, because chelatable Zn2+ plays important roles in many biological systems. Lanthanicle complexes (Eu3+, Tb3+, etc.) have excellent spectroscopic properties for biological applications, such as long luminescence lifetimes of the order of milliseconds, a large Stoke's shift of >200 nm, and high water solubility. Herein, we present the design and synthesis of a novel lanthanide sensor molecule, [Eu-7], for detecting Zn2+. This europium (Eu3+) complex employs a quinolyl ligand as both a chromophore and an acceptor for Zn2+. Upon addition of Zn2+ to a solution of [Eu-7], the luminescence of Eu3+ is strongly enhanced, with high selectivity for Zn2+ over other biologically relevant metal cations. One of the important advantages of [Eu-7] is that this complex can be excited with longer excitation wavelengths (around 340 nm) as compared with previously reported Zn2+-sensitive luminescent lamthanide sensors, whose excitation wavelength is at too high an energy level for biological applications. The usefulness of [Eu-7] for monitoring Zn2+ changes in living HeLa cells was confirmed. This novel Zn2+-selective luminescent lanthanide chemosensor [Eu-7] should be an excellent lead compound for the development of a range of novel luminescent lanthanide chemosensors for biological applications.

  DOI：

  10.1021/ja0469333