2,3-bis-(2-methyl-1H-indol-3-yl)-N-methylmaleimide | 119139-15-0

• 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: 2,3-bis-(2-methyl-1H-indol-3-yl)-N-methylmaleimide
• 英文别名: 2,3-bis(2-methyl-1H-indol-3-yl)-N-methylmaleimide；N-methyl-2,3-bis(2-methyl-1H-indol-3-yl)maleimide；1-Methyl-3,4-bis(2-methyl-1h-indol-3-yl)-1h-pyrrole-2,5-dione；1-methyl-3,4-bis(2-methyl-1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 119139-15-0
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: GMJNOBULFLLYKL-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  658.6±55.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二溴-N-甲基马来酰亚胺 生成 2,3-bis-(2-methyl-1H-indol-3-yl)-N-methylmaleimide
  参考文献：
  名称：

  BRENNER, MICHAEL;REXHAUSEN, HANS;STEFFAN, BERT;STEGLICH, WOLFGANG, TETRAHEDRON, 44,(1988) N 10, 2887-2892

  摘要：

  DOI：

文献信息

• Pyrrole derivatives and cell death inhibitors
  申请人：Sagami Chemical Research Center

  公开号：US06589977B1

  公开（公告）日：2003-07-08

  Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death participates; and cell death inhibitors, drugs and cell/tissue/organ preservatives containing as the active ingredient these derivatives or pharmaceutically acceptable salts thereof.

  一般公式为[I]的双吲哚吡咯衍生物在抑制细胞死亡方面具有用处，并被期望作为预防和治疗各种疾病进展中细胞死亡参与的进展和恶化的药物；以及包含这些衍生物或其药学上可接受的盐作为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官保护剂。
• A General Approach to the Synthesis of Bisindolylmaleimides: Synthesis of Staurosporine Aglycone
  作者：Margaret M. Faul、Kevin A. Sullivan、Leonard L. Winneroski

  DOI：10.1055/s-1995-4146

  日期：1995.12

  Bisindolylmaleimides are prepared in 65-95% yield by reaction of an indole Grignard with either 2,3-dichloro-N-methylmaleimide or 2,3-dichloromaleimide. A one-step synthesis of arcyriarubin A in 72% yield affords ready access to the staurosporine aglycone.

  双吲哚马来酰亚胺是通过吲哚格氏化合物与 2,3-二氯-N-甲基马来酰亚胺或 2,3-二氯马来酰亚胺反应制备的，收率为 65-95%。一步法合成 arcyriarubin A 的收率为 72%，可直接获得石杉碱苷苷元。
• PYRROLE DERIVATIVES AND CELL DEATH INHIBITORS
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1152002A1

  公开（公告）日：2001-11-07

  Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death participates; and cell death inhibitors, drugs and cell/tissue/organ preservatives containing as the active ingredient these derivatives or pharmaceutically acceptable salts thereof.

  由通式[I]表示的双吲哚基吡咯衍生物，可用于抑制细胞死亡，并可望作为预防和治疗细胞死亡导致的各种疾病的进展和恶化的药物；以及含有这些衍生物或其药学上可接受的盐类作为活性成分的细胞死亡抑制剂、药物和细胞/组织/器官防腐剂。
• Use of maleimide derivatives for preventing and treating cancer
  申请人：CENTOGENE AG

  公开号：US10420754B2

  公开（公告）日：2019-09-24

  The present invention is related to a compound of formula (I): a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, a metabolite thereof or a prodrug thereof; for use in a method for the treatment and/or prevention of cancer, wherein X is selected from the group consisting of N—R1, O and S; R1 is selected from the group consisting of alkyl, cycloalkyl, aryl, arylalkyl and hydrogen; R2 is selected from the group consisting of indolyl, substituted indolyl, azaindolyl and substituted azaindolyl; and R3 is selected from the group consisting of aryl, substituted aryl, unsubstituted heteroaryl, heterocyclyl and substituted heterocyclyl.

  本发明涉及一种式（I）化合物： 其药学上可接受的盐、其水合物、其溶液、其代谢物或其原药； 用于治疗和/或预防癌症的方法，其中 X选自由N-R1、O和S组成的组； R1 选自由烷基、环烷基、芳基、芳烷基和氢组成的组； R2 选自由吲哚基、取代的吲哚基、偶氮吲哚基和取代的偶氮吲哚基组成的组；和 R3 选自由芳基、取代的芳基、未取代的杂芳基、杂环基和取代的杂环基组成的组。
• Structure–activity relationship of N-methyl-bisindolylmaleimide derivatives as cell death inhibitors
  作者：Miho Katoh、Kosuke Dodo、Mikako Fujita、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2005.04.015

  日期：2005.6

  A series of N-methyl-bisindolylmaleimide derivatives was synthesized and evaluated as cell death inhibitors. N-Methyl-2[1-(3-aminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleimide (21) was the most potent inhibitor of H2O2-induced necrotic death of human leukemia HL60 cells among them. (c) 2005 Elsevier Ltd. All rights reserved.