3-(indol-1-yl)-4-(indol-3-yl)maleimide | 374817-51-3

• 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: 3-(indol-1-yl)-4-(indol-3-yl)maleimide
• 英文别名: 3-(indol-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione；1H-Pyrrole-2,5-dione, 3-(1H-indol-1-yl)-4-(1H-indol-3-yl)-；3-indol-1-yl-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 374817-51-3
• 化学式: C₂₀H₁₃N₃O₂
• 分子量: 327.342
• InChiKey: TZGKDMNBGRNSCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  524.8±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(indol-1-yl)-4-(indol-3-yl)maleimide 在 甲烷磺酸 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以56%的产率得到8b,9-dihydroindolo[4',3':3,4,5]pyrrolo[3',4':6,7]azepino[1,2-a]indole-1,3(2H,5H)-dione
  参考文献：
  名称：

  Synthesis of 4-substituted 3-(indol-3-yl)maleimides and azepines with annelated indole and maleimide nuclei

  摘要：

  A series of 4-substituted 3-(indole-3-yl)maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H, 8H)-dione derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.027
• 作为产物：
  描述：

  吲哚啉 在 potassium tert-butylate 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 5.0h， 生成 3-(indol-1-yl)-4-(indol-3-yl)maleimide
  参考文献：
  名称：

  Synthesis of 4-substituted 3-(indol-3-yl)maleimides and azepines with annelated indole and maleimide nuclei

  摘要：

  A series of 4-substituted 3-(indole-3-yl)maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H, 8H)-dione derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.027

文献信息

• Neuroprotective and anti-proliferative compounds
  申请人：——

  公开号：US20040102467A1

  公开（公告）日：2004-05-27

  This invention features ring-substituted pyrrolo-&bgr;-carboline derivatives and ring-substitution and structural derivatives of 3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione of formulas (I-III), which are useful as neuroprotective and anti-proliferative compounds. Also disclosed are methods for the preparation of these compounds, selected biological profiles and uses of these compounds in the treatment of various neurodegenerative and inflammatory diseases of the human nervous system and in the treatment of various other proliferative disorders characterized by loss of growth or cellular differentiation control including, but not limited to, cancer and inflammation. 1

  这项发明涉及环取代吡咯β-咔啉衍生物和3-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮的环取代和结构衍生物，其作为神经保护和抗增殖化合物具有用途。还公开了这些化合物的制备方法，选择的生物学特性以及这些化合物在治疗人类神经系统的各种神经退行性和炎症性疾病以及治疗其他各种增殖性疾病中的用途，这些疾病的特征是失去生长或细胞分化控制，包括但不限于癌症和炎症。
• NEUROPROTECTIVE AND ANTI-PROLIFERATIVE COMPOUNDS
  申请人：Aegera Therapeutics Inc.

  公开号：EP1283836A2

  公开（公告）日：2003-02-19
• US7129250B2
  申请人：——

  公开号：US7129250B2

  公开（公告）日：2006-10-31
• [EN] NEUROPROTECTIVE AND ANTI-PROLIFERATIVE COMPOUNDS<br/>[FR] COMPOSÉS NEUROPROTECTEURS ET ANTI-PROLIFÉRATIFS
  申请人：AEGERA THERAPEUTICS INC

  公开号：WO2001087887A2

  公开（公告）日：2001-11-22

  This invention features ring-substituted pyrrolo-β-carboline derivatives and ring-substitution and structural derivatives of 3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione of formulas (I - III), which are useful as neuroprotective and anti-proliferative compounds. Also disclosed are methods for the preparation of these compounds, selected biological profiles and uses of these compounds in the treatment of various neurodegenerative and inflammatory diseases of the human nervous system and in the treatment of various other proliferative disorders characterized by loss of growth or cellular differentiation control including, but not limited to, cancer and inflammation.
• [EN] NEUROPROTECTIVE AND ANTI-PROLIFERATIVE COMPOUNDS<br/>[FR] COMPOSES NEUROPROTECTEURS ET ANTIPROLIFERATIFS
  申请人：AEGERA THERAPEUTICS INC

  公开号：WO2005014584A1

  公开（公告）日：2005-02-17

  This invention features compounds of formula (I), (II) and (III), which are useful in the treatment of proliferative disorders characterized by loss of growth or cellular differentiation control including, but not limited to, cancer and inflammation. Formulas (I), (II), (III) have functional groups designated as A1, A2, B1, B2, X1-X9 and Rl -R8 as defined further.