4-bromo-N-butyl-3-(2-methylindol-3-yl)maleimide | 894428-73-0

• 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: 4-bromo-N-butyl-3-(2-methylindol-3-yl)maleimide
• CAS: 894428-73-0
• 化学式: C₁₇H₁₇BrN₂O₂
• 分子量: 361.238
• InChiKey: LOPVTSYCOMKMEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-bromo-N-butyl-3-(2-methylindol-3-yl)maleimide 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 正丁胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 N-butyl-3-(2-methyl-1-benzothiophen-3-yl)-4-(2-methyl-1H-indol-3-yl)maleimide
  参考文献：
  名称：

  A convenient synthesis of 3,4-diaryl(hetaryl)-substituted maleimides and maleic anhydrides

  摘要：

  A convenient procedure has been developed for the synthesis of 3,4-diaryl(or hetaryl)maleimides by cross coupling of N-substituted 3,4-dibromomaleimides with aryl(hetaryl)boronic acids in the presence of Pd(Ph3P)(4) and CsF The reaction ensures high yields of the products and requires relatively small amount of the catalyst; it can be performed on an enlarged scale. The resulting maleimides are readily converted into the corresponding maleic anhydrides.

  DOI：

  10.1134/s1070428006100162
• 作为产物：
  描述：

  N-正丁基马来酰亚胺 在 溴 、 sodium acetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.25h， 生成 4-bromo-N-butyl-3-(2-methylindol-3-yl)maleimide
  参考文献：
  名称：

  A convenient synthesis of 3,4-diaryl(hetaryl)-substituted maleimides and maleic anhydrides

  摘要：

  A convenient procedure has been developed for the synthesis of 3,4-diaryl(or hetaryl)maleimides by cross coupling of N-substituted 3,4-dibromomaleimides with aryl(hetaryl)boronic acids in the presence of Pd(Ph3P)(4) and CsF The reaction ensures high yields of the products and requires relatively small amount of the catalyst; it can be performed on an enlarged scale. The resulting maleimides are readily converted into the corresponding maleic anhydrides.

  DOI：

  10.1134/s1070428006100162

文献信息

• Novel indolylmaleimide acts as GSK-3β inhibitor in human neural progenitor cells
  作者：Anne-Caroline Schmöle、Anne Brennführer、Gnuni Karapetyan、Robert Jaster、Anahit Pews-Davtyan、Rayk Hübner、Stefanie Ortinau、Matthias Beller、Arndt Rolfs、Moritz J. Frech

  DOI：10.1016/j.bmc.2010.07.045

  日期：2010.9

  The Wnt pathway is involved in cellular processes linked to either proliferation or differentiation. Therefore small molecules offer an attractive opportunity to modulate this pathway, whereas the key enzyme GSK-3 beta is of special interest. In this study, non-symmetrically substituted indolylmaleimides have been synthesized and their ability to function as GSK-3 beta inhibitors has been investigated in a human neural progenitor cell line. Among the newly synthesized compounds, the substance IM-12 showed a significant activity in several biological tests which was comparable or even outplayed the effects of the known GSK-3 beta inhibitor SB-216763. Furthermore the treatment of human neural progenitor cells with IM-12 resulted in an increase of neuronal cells. Therefore we conclude that indolylmaleimides act via the canonical Wnt signalling pathway by inhibition of the key enzyme GSK-3 beta. (C) 2010 Elsevier Ltd. All rights reserved.