3-(bromomethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione | 1433758-32-7

• 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-(bromomethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
• 英文别名: 3-(Bromomethyl)-5-methoxy-1,2-dimethylindole-4,7-dione
• CAS: 1433758-32-7
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: XFKFQOHWDJAIBL-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione 、 sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 在 15-冠醚-5 作用下， 以 四氢呋喃 为溶剂， 反应 6.25h， 以15 mg的产率得到2-methyl-3-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato-methyl]-5-methoxy-1-methyl-1H-indole-4,7-dione
  参考文献：
  名称：

  INDQ/NO, a Bioreductively Activated Nitric Oxide Prodrug

  摘要：

  The design, synthesis, and development of INDQ/NO, a novel nitric oxide (NO) prodrug targeted by a bioreductive trigger, are described. INDQ/NO, an indolequinone-diazeniumdiolate is found to be metabolized to produce NO by DT-diaphorase, a bioreductive enzyme that is overexpressed in certain cancers and hypoxic tumors. Cell-based assays revealed that INDQ/NO induces DNA damage and is a potent inhibitor of cancer cell proliferation.

  DOI：

  10.1021/ol400884v
• 作为产物：
  描述：

  3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 3-(bromomethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
  参考文献：
  名称：

  INDQ/NO, a Bioreductively Activated Nitric Oxide Prodrug

  摘要：

  The design, synthesis, and development of INDQ/NO, a novel nitric oxide (NO) prodrug targeted by a bioreductive trigger, are described. INDQ/NO, an indolequinone-diazeniumdiolate is found to be metabolized to produce NO by DT-diaphorase, a bioreductive enzyme that is overexpressed in certain cancers and hypoxic tumors. Cell-based assays revealed that INDQ/NO induces DNA damage and is a potent inhibitor of cancer cell proliferation.

  DOI：

  10.1021/ol400884v