2,3-bis(1-tosyl-indol-3-yl)-N-methylmaleimide | 1207184-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-bis(1-tosyl-indol-3-yl)-N-methylmaleimide
• 英文别名: 1-Methyl-3,4-bis[1-(4-methylphenyl)sulfonylindol-3-yl]pyrrole-2,5-dione
• CAS: 1207184-82-4
• 化学式: C₃₅H₂₇N₃O₆S₂
• 分子量: 649.748
• InChiKey: VMGABEXZNNVHEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis(1-tosyl-indol-3-yl)-N-methylmaleimide 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以84%的产率得到双吲哚马来酰亚胺 V
  参考文献：
  名称：

  Synthesis of Arcyriarubin A and Arcyriaflavin A via Cross-Coupling of Indolylboronic Acid with Dibromomaleimides

  摘要：

  Arcyriarubin A was first isolated by Steglich in 1980; it is also the key intermediate in the synthesis of indolocarbazole compounds. A new synthetic approach to the natural products arcyriaflavin A and arcyriarubin A is described. The key step is a Suzuki cross-coupling reaction using indolylboronic acid as the starting material. The preparation of arcyriaflavin A was accomplished in eight steps from indole for a total yield of 21%.

  DOI：

  10.1080/00397910902962878
• 作为产物：
  描述：

  2,3-二溴-N-甲基马来酰亚胺 、 1-甲苯基-3-吲哚硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 10.0h， 以52%的产率得到2,3-bis(1-tosyl-indol-3-yl)-N-methylmaleimide
  参考文献：
  名称：

  Synthesis of Arcyriarubin A and Arcyriaflavin A via Cross-Coupling of Indolylboronic Acid with Dibromomaleimides

  摘要：

  Arcyriarubin A was first isolated by Steglich in 1980; it is also the key intermediate in the synthesis of indolocarbazole compounds. A new synthetic approach to the natural products arcyriaflavin A and arcyriarubin A is described. The key step is a Suzuki cross-coupling reaction using indolylboronic acid as the starting material. The preparation of arcyriaflavin A was accomplished in eight steps from indole for a total yield of 21%.

  DOI：

  10.1080/00397910902962878

文献信息

• Synthesis of Arcyriarubin A and Arcyriaflavin A via Cross-Coupling of Indolylboronic Acid with Dibromomaleimides
  作者：Ke Wang、Zhanzhu Liu

  DOI：10.1080/00397910902962878

  日期：2009.12.15

  Arcyriarubin A was first isolated by Steglich in 1980; it is also the key intermediate in the synthesis of indolocarbazole compounds. A new synthetic approach to the natural products arcyriaflavin A and arcyriarubin A is described. The key step is a Suzuki cross-coupling reaction using indolylboronic acid as the starting material. The preparation of arcyriaflavin A was accomplished in eight steps from indole for a total yield of 21%.
• Synthesis and antitumor activity of bisindolylmaleimide and amino acid ester conjugates
  作者：Ke Wang、Xiang-Yan Li、Xiao-Guang Chen、Zhan-Zhu Liu

  DOI：10.1080/10286020903413385

  日期：2010.1.1

  A series of novel bisindolylmaleimide and natural amino acid ester conjugates were synthesized and evaluated for their inhibitory activity against six tumor cell lines. Some compounds displayed interesting cytotoxic profiles. The most active compound 8e showed inhibitory activity against several human cancer cell lines.