2-ethoxycarbonyl-N-methyl-3-(2-methyl-1H-indol-3-yl)maleimide | 1129668-84-3

• 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-ethoxycarbonyl-N-methyl-3-(2-methyl-1H-indol-3-yl)maleimide
• 英文别名: ethyl 1-methyl-4-(2-methyl-1H-indol-3-yl)-2,5-dioxopyrrole-3-carboxylate
• CAS: 1129668-84-3
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: YTHADCYGIFZPCK-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  527.0±50.0 °C(predicted)
• 密度：
  1.363±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-methyl-3-bromo-4-(2-methyl-1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione 、 乙醇 、 一氧化碳 在 palladium diacetate 、 正丁基二(1-金刚烷基)膦 作用下， 生成 2-ethoxycarbonyl-N-methyl-3-(2-methyl-1H-indol-3-yl)maleimide
  参考文献：
  名称：

  Novel indolylmaleimide acts as GSK-3β inhibitor in human neural progenitor cells

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.07.045

文献信息

• Catalytic and Stoichiometric Synthesis of Novel 3-Aminocarbonyl-, 3-Alkoxycarbonyl-, and 3-Amino-4-indolylmaleimides
  作者：Anne Brennführer、Helfried Neumann、Anahit Pews-Davtyan、Matthias Beller

  DOI：10.1002/ejoc.200800964

  日期：——

  Novel nonsymmetrically substituted 4-indolylmaleimides have been synthesized via palladium-catalyzed alkoxy- and aminocarbonylation of 3-bromo-1-methyl-4-(2-methyl-3-indolyl)maleimide (1) with alcohols and amines in the presence of carbon monoxide. The resulting carboxamide derivatives represent a new class of potentially bioactive compounds. In addition, the direct amination reaction of 1 proceeded

  在碳存在下，通过钯催化的烷氧基和氨基羰基化 3-溴-1-甲基-4-（2-甲基-3-吲哚基）马来酰亚胺（1）与醇和胺，合成了新型的非对称取代的 4-吲哚基马来酰亚胺一氧化氮。由此产生的甲酰胺衍生物代表了一类新的潜在生物活性化合物。此外，1 的直接胺化反应在没有催化剂的情况下顺利进行，并以良好的产率得到所需的 3-氨基-4-吲哚基马来酰亚胺。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）