{4-amino-5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indol-3-yl}methanol | 1173188-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: {4-amino-5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indol-3-yl}methanol
• CAS: 1173188-88-9
• 化学式: C₂₂H₃₈N₂O₃Si
• 分子量: 406.641
• InChiKey: CHDTYZPRRQTWLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.64
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {4-amino-5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indol-3-yl}methanol 在 sodium dihydrogenphosphate 、 potassium nitrososulfonate 、 水 、 甲基三辛基氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以3.52 g的产率得到5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-3-hydroxymethyl-1,2-dimethyl-1H-indole-4,7-dione
  参考文献：
  名称：

  Preparation and fluorescence properties of fluorophore-labeled avidin–biotin system immobilized on Fe3O4 nanoparticles through functional indolequinone linker

  摘要：

  We prepared and characterized a new class of fluorophore-labeled magnetic nanoparticles (MNPs) possessing a hypoxia-responsive unit to construct a hypoxia-selective emission system. The indolequinone derivative as a hypoxia-response unit bearing biotin was synthesized and immobilized on Fe3O4 MNP. Subsequent complexation of this functionalized MNP with fluorescein-labeled avidin formed fluorophore-labeled nanoparticles (AF-QB@MNP). The fluorescence intensity of AF-QB@MNP was suppressed because of the adjacent quenching function of the indolequinone moiety and MNP. Upon hypoxic treatment by NADPH: cytochrome P450 reductase, AF-QB@MNP was activated to liberate a fluorescence unit, leading to the significant enhancement of fluorescence emission, while a smaller enhancement in fluorescence emission occurred upon aerobic treatment. The AF-QB@MNP has a indispensable properties as a fluorescent probe for imaging of disease relevant hypoxic microenvironments. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.048
• 作为产物：
  描述：

  4-amino-5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 {4-amino-5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indol-3-yl}methanol
  参考文献：
  名称：

  Preparation and fluorescence properties of fluorophore-labeled avidin–biotin system immobilized on Fe3O4 nanoparticles through functional indolequinone linker

  摘要：

  We prepared and characterized a new class of fluorophore-labeled magnetic nanoparticles (MNPs) possessing a hypoxia-responsive unit to construct a hypoxia-selective emission system. The indolequinone derivative as a hypoxia-response unit bearing biotin was synthesized and immobilized on Fe3O4 MNP. Subsequent complexation of this functionalized MNP with fluorescein-labeled avidin formed fluorophore-labeled nanoparticles (AF-QB@MNP). The fluorescence intensity of AF-QB@MNP was suppressed because of the adjacent quenching function of the indolequinone moiety and MNP. Upon hypoxic treatment by NADPH: cytochrome P450 reductase, AF-QB@MNP was activated to liberate a fluorescence unit, leading to the significant enhancement of fluorescence emission, while a smaller enhancement in fluorescence emission occurred upon aerobic treatment. The AF-QB@MNP has a indispensable properties as a fluorescent probe for imaging of disease relevant hypoxic microenvironments. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.048