2-[[吡啶-2-基甲基(噻吩-2-基甲基)氨基]甲基]苯酚 | 918423-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[[吡啶-2-基甲基(噻吩-2-基甲基)氨基]甲基]苯酚
• 英文名称: 2-{(pyridin-2-ylmethylthiophen-2ylmethylamino)methyl}phenol
• 英文别名: 2-({[(Pyridin-2-yl)methyl][(thiophen-2-yl)methyl]amino}methyl)phenol；2-[[pyridin-2-ylmethyl(thiophen-2-ylmethyl)amino]methyl]phenol
• CAS: 918423-93-5
• 化学式: C₁₈H₁₈N₂OS
• 分子量: 310.42
• InChiKey: DUTNVAGHSPVHTE-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  437.7±40.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻甲基苄醇 、 1-(pyridin-2-yl)-N-(thiophen-2-ylmethyl)methanamine 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 以61%的产率得到2-[[吡啶-2-基甲基(噻吩-2-基甲基)氨基]甲基]苯酚
  参考文献：
  名称：

  Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization

  摘要：

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-{6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.

  DOI：

  10.1021/ja065759a

文献信息

• Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization
  作者：Elizabeth M. Nolan、Jubin W. Ryu、Jacek Jaworski、Rodney P. Feazell、Morgan Sheng、Stephen J. Lippard

  DOI：10.1021/ja065759a

  日期：2006.12.1

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.