2-[2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]-isoindole-1,3-dione | 1012370-05-6

• 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: 2-[2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]-isoindole-1,3-dione
• 英文别名: 2-[2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]isoindole-1,3-dione
• CAS: 1012370-05-6
• 化学式: C₂₆H₂₀N₂O₆
• 分子量: 456.455
• InChiKey: LVKOXOXDMJKIGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]-isoindole-1,3-dione 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到2-[2-(3,4,5-trimethoxybenzoyl)-1-methyl-indol-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Methyl-2-(3′,4′,5′-trimethoxybenzoyl)-3-aminoindoles as a New Class of Antimitotic Agents and Tubulin Inhibitors

  摘要：

  The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent anti proliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.

  DOI：

  10.1021/jm7011547
• 作为产物：
  描述：

  (3-amino-1H-indol-2-yl)-(3,4,5-trimethoxy-phenyl)methanone 、 苯酐 在 溶剂黄146 作用下， 反应 18.0h， 以75%的产率得到2-[2-(3,4,5-trimethoxybenzoyl)-1H-indol-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Methyl-2-(3′,4′,5′-trimethoxybenzoyl)-3-aminoindoles as a New Class of Antimitotic Agents and Tubulin Inhibitors

  摘要：

  The 2-(3,4,5-trimethoxybenzoyl)-2-aminoindole nucleus was used as the fundamental structure for the synthesis of compounds modified with respect to positions C-4 to C-7 with different moieties (chloro, methyl, or methoxy). Additional structural variations concerned the indole nitrogen, which was alkylated with small alkyl groups such as methyl or ethyl. We have identified 1-methyl-2-(3,4,5-trimethoxybenzoyl)-3-amino-7-methoxyindole as a new highly potent anti proliferative agent that targets tubulin at the colchicine binding site and leads to apoptotic cell death.

  DOI：

  10.1021/jm7011547