3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione | 570431-85-5

• 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: 3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione
• 英文别名: 2-bromo-3-(indol-1-yl)maleimide；3-bromo-4-indol-1-ylpyrrole-2,5-dione
• CAS: 570431-85-5
• 化学式: C₁₂H₇BrN₂O₂
• 分子量: 291.104
• InChiKey: BEHYVQAQUFEYAR-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±42.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione 在 氨 作用下， 以 甲醇 为溶剂， 以80%的产率得到2-amino-3-(indol-1-yl)maleimide
  参考文献：
  名称：

  Synthesis of 2-hetaryl-3-(indol-1-yl)-and -(3-pyrrol-1-yl)maleimides and study of their conversions under the action of protic acids*

  摘要：

  A series of 3-(indol-1-yl)maleimides has been synthesized, substituted at position 2 by residues of amines or various nitrogenous heterocycles. The possibility of obtaining new polycondensed heterocyclic structures from them has been studied. Experimental investigations confirmed theoretical predictions made on the basis of results of quantum-chemical calculations.

  DOI：

  10.1007/s10593-011-0656-9
• 作为产物：
  描述：

  吲哚啉 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-bromo-4-(1H-indol-1-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of 6H-pyrrolo[3′,4′:2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold

  摘要：

  合成了一系列 3-芳烷基或 3-烷基氨基-4-(吲哚-1-基)马来酰亚胺和双(吲哚-1-基)马来酰亚胺。在酸的作用下，3-取代的 4-(吲哚-1-基)马来酰亚胺环化，形成了吲哚啉和马来酰亚胺核环化的二氮杂卓[1,4]衍生物。这些化合物在脱氢后很容易生成相应的吲哚马来酰亚胺二氮杂卓[1,4]。

  DOI：

  10.1039/b211163b

文献信息

• New 3,4-bis(indol-1-yl)maleimides as protein kinase inhibitors
  作者：Alexey A. Panov、Sergey A. Lakatosh、Michael H. G. Kubbutat、Lyubov G. Dezhenkova、Frank Totzke、Kristof Schechtel

  DOI：10.1007/s10593-019-02576-5

  日期：2019.11

  Several previously unknown derivatives of 3,4-bis(indol-1-yl)maleimide, as well as 3-(2,3-dihydroindol-1-yl)-4-(indol-1-yl)maleimide were synthesized as potential analogs for a known series of protein kinase inhibitors BIS I, IV, IX containing the structural motif of 3,4-bis(indol-3-yl)maleimide. The activity of these synthesized compounds was characterized with regard to several human protein kinases and their cytotoxicity was determined.
• Synthesis of 6H-pyrrolo[3′,4′:2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold
  作者：Sergey A. Lakatosh、Yuri N. Luzikov、Maria N. Preobrazhenskaya

  DOI：10.1039/b211163b

  日期：2003.2.27

  Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)maleimides and bis(indol-1-yl)maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and maleimide nuclei annelated. These compounds readily produced the corresponding indolomaleimidodiazepines[1,4] after dehydrogenation.

  合成了一系列 3-芳烷基或 3-烷基氨基-4-(吲哚-1-基)马来酰亚胺和双(吲哚-1-基)马来酰亚胺。在酸的作用下，3-取代的 4-(吲哚-1-基)马来酰亚胺环化，形成了吲哚啉和马来酰亚胺核环化的二氮杂卓[1,4]衍生物。这些化合物在脱氢后很容易生成相应的吲哚马来酰亚胺二氮杂卓[1,4]。
• Synthesis of 2-hetaryl-3-(indol-1-yl)-and -(3-pyrrol-1-yl)maleimides and study of their conversions under the action of protic acids*
  作者：S. A. Lakatosh、E. E. Bykov、M. N. Preobrazhenskaya

  DOI：10.1007/s10593-011-0656-9

  日期：2011.1

  A series of 3-(indol-1-yl)maleimides has been synthesized, substituted at position 2 by residues of amines or various nitrogenous heterocycles. The possibility of obtaining new polycondensed heterocyclic structures from them has been studied. Experimental investigations confirmed theoretical predictions made on the basis of results of quantum-chemical calculations.