3-(1-acetyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

• 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-(1-acetyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione
• 英文别名: 3-(1-Acetylindol-3-yl)-4-(1-methylindol-3-yl)pyrrole-2,5-dione
• 化学式: C₂₃H₁₇N₃O₃
• 分子量: 383.406
• InChiKey: GKPCNOFSKUITFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-methylindole-3-glyoxylyl chloride 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3-(1-acetyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  A convenient synthesis of bisindolylmaleimides

  摘要：

  A mild and flexible method for the preparation of bisindolylmaleimides from the corresponding indoles and indole-3-acetimidate esters is described.

  DOI：

  10.1016/s0040-4039(00)73899-8

文献信息

• Process for the preparation of 2-substituted and 2,3-disubstituted
  申请人：Hoffmann-La Roche Inc.

  公开号：US05399712A1

  公开（公告）日：1995-03-21

  The invention relates to a process for the manufacture of substituted maleimides of the formula ##STR1## wherein R.sup.1 is alkyl, aryl or heteroaryl and R.sup.2 is hydrogen, alkyl, alkoxycarbonyl, aryl or heteroaryl, by reacting an activated glyoxylate of the formula ##STR2## wherein R.sup.1 has the above significance and X is a leaving atom or group, with an imidate of the formula ##STR3## wherein R.sup.2 has the above significance, R.sup.3 is alkyl, aryl or trialkylsilyl and Y is oxygen or sulfur, in the presence of a base and, after treating the resulting reaction product obtained in which R.sup.2 is hydrogen or alkyl with a strong base, hydrolyzing and dehydrating the resulting hydroxy-pyrrolinone of the formula ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and Y have the above significance. The substituted maleimides of formula I are pharmacologically active, for example as protein kinase C inhibitors and which a useful, for example, in the treatment and prophylaxis of inflammatory, immunological, bronchopulmonary and cardiovascular disorders, or as antiproliferative agents useful, for example, in the treatment of immune diseases and allergic disorders.

  该发明涉及一种制备式为##STR1##的取代马来酰亚胺的方法，其中R.sup.1是烷基、芳基或杂环芳基，R.sup.2是氢、烷基、烷氧羰基、芳基或杂环芳基，通过将式为##STR2##的活化的甘醇酸酯与式为##STR3##的亚胺在碱存在下反应，其中R.sup.1具有上述含义，X是一个脱离原子或基团，然后处理所得的反应产物，其中R.sup.2是氢或烷基，用强碱处理后，水解和脱水所得的式为##STR4##的羟基吡咯烷酮，其中R.sup.1、R.sup.2、R.sup.3和Y具有上述含义。式I的取代马来酰亚胺在药理学上具有活性，例如作为蛋白激酶C抑制剂，可用于治疗和预防炎症、免疫、支气管肺部和心血管疾病，或作为抗增殖剂，例如用于治疗免疫性疾病和过敏性疾病。
• Process for the manufacture of substituted maleimides
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0540956B1

  公开（公告）日：1997-09-03
• US5399712A
  申请人：——

  公开号：US5399712A

  公开（公告）日：1995-03-21
• A convenient synthesis of bisindolylmaleimides
  作者：Rino A. Bit、Peter H. Crackett、William Harris、Christopher H. Hill

  DOI：10.1016/s0040-4039(00)73899-8

  日期：1993.8

  A mild and flexible method for the preparation of bisindolylmaleimides from the corresponding indoles and indole-3-acetimidate esters is described.