5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester | 1173188-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester
• CAS: 1173188-84-5
• 化学式: C₂₃H₃₇NO₄Si
• 分子量: 419.637
• InChiKey: DXODPOWYCAUNGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.69
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester 在 硝酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到5-(5-hydroxypentoxy)-1,2-dimethyl-4-nitro-1H-indole-3-carboxylic acid methyl ester
  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：

  ethyl 5-hydroxy-2-methylindole-3-carboxylate 、 1-bromo-5-(tert-butyldimethylsilyloxy)pentane 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以38%的产率得到5-[5-(tert-butyldimethylsilanyloxy)pentoxy]-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester
  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