3-(hydroxymethyl)-5-(methoxy-13C)-1,2-dimethyl-1H-indole-4,7-dione | 1271786-89-0

• 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: 3-(hydroxymethyl)-5-(methoxy-13C)-1,2-dimethyl-1H-indole-4,7-dione
• CAS: 1271786-89-0
• 化学式: C₁₂H₁₃NO₄
• 分子量: 236.229
• InChiKey: OGNGGVGRGMBLMA-LBPDFUHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  二乙烯三胺五醋酸 、 3-(hydroxymethyl)-5-(methoxy-13C)-1,2-dimethyl-1H-indole-4,7-dione 在 4-二甲氨基吡啶 、 TATU 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  13C-labeled indolequinone-DTPA-Gd conjugate for NMR probing cytochrome:P450 reductase-mediated one-electron reduction

  摘要：

  We designed and synthesized a new class of C-13-labeled NMR probe, C-13-IQ-Gd, to monitor one-electron reductions by cytochrome: P450 (CYP450) reductase under hypoxic conditions. C-13-IQ-Gd consisted of a Gd3+-diethylene triamine pentaacetic acid (DTPA) complex unit and an indolequinone (C-13-IQ) unit bearing a C-13-labeled methoxy group. The C-13 NMR signal of C-13-IQ-Gd was suppressed because of the intramolecular paramagnetic effect of Gd3+, whereas enzymatic reduction mediated by CYP450 reductase under hypoxic conditions yielded an intensed C-13 NMR signal due to enzymatic activation of the IQ unit followed by release of the DTPA-Gd unit from C-13-IQ-Gd. This C-13 NMR spectral change allowed the monitoring of CYP450 reducatase-mediated one-electron reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.105
• 作为产物：
  描述：

  在 sodium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 水 、 丙酮 为溶剂， 生成 3-(hydroxymethyl)-5-(methoxy-13C)-1,2-dimethyl-1H-indole-4,7-dione
  参考文献：
  名称：

  13C-labeled indolequinone-DTPA-Gd conjugate for NMR probing cytochrome:P450 reductase-mediated one-electron reduction

  摘要：

  We designed and synthesized a new class of C-13-labeled NMR probe, C-13-IQ-Gd, to monitor one-electron reductions by cytochrome: P450 (CYP450) reductase under hypoxic conditions. C-13-IQ-Gd consisted of a Gd3+-diethylene triamine pentaacetic acid (DTPA) complex unit and an indolequinone (C-13-IQ) unit bearing a C-13-labeled methoxy group. The C-13 NMR signal of C-13-IQ-Gd was suppressed because of the intramolecular paramagnetic effect of Gd3+, whereas enzymatic reduction mediated by CYP450 reductase under hypoxic conditions yielded an intensed C-13 NMR signal due to enzymatic activation of the IQ unit followed by release of the DTPA-Gd unit from C-13-IQ-Gd. This C-13 NMR spectral change allowed the monitoring of CYP450 reducatase-mediated one-electron reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.105