(3E)-3-benzylidene-6-bromo-1H-indol-2-one | 865079-94-3

• 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: (3E)-3-benzylidene-6-bromo-1H-indol-2-one
• CAS: 865079-94-3
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: HVFHCEOIYNZUEC-MDWZMJQESA-N

物化性质

• 沸点：
  464.5±45.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3E)-3-benzylidene-6-bromo-1H-indol-2-one 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 (2'R,3'S,4'R,5'R)-6-Bromo-1'-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-2'-isobutyl-2-oxo-4'-phenyl-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid dimethylamide
  参考文献：
  名称：

  Synthesis of spirooxindoles via asymmetric 1,3-dipolar cycloaddition

  摘要：

  An efficient method was developed for the asymmetric synthesis of 2'-alkyl-4'aryl-1H-spiro[indole-3,3'-pyrrolidin]-2-ones, which are potential inhibitors of the p53-MDM2 interaction. Our X-ray crystallographic analysis revealed that this 1,3-dipolar cycloaddition proceeds with high stereoselectivity but differently from previously published results. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.114
• 作为产物：
  描述：

  苯甲醛 、 6-溴-2-羟吲哚 在 aluminum oxide 、 potassium fluoride 作用下， 反应 0.08h， 以60%的产率得到(3E)-3-benzylidene-6-bromo-1H-indol-2-one
  参考文献：
  名称：

  Synthesis of spirooxindoles via asymmetric 1,3-dipolar cycloaddition

  摘要：

  An efficient method was developed for the asymmetric synthesis of 2'-alkyl-4'aryl-1H-spiro[indole-3,3'-pyrrolidin]-2-ones, which are potential inhibitors of the p53-MDM2 interaction. Our X-ray crystallographic analysis revealed that this 1,3-dipolar cycloaddition proceeds with high stereoselectivity but differently from previously published results. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.114

文献信息

• Small molecule inhibitors of MDM2 and the uses thereof
  申请人：Wang Shaomeng

  公开号：US20060211757A1

  公开（公告）日：2006-09-21

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  这项发明涉及小分子，其作为p53和MDM2之间相互作用的抑制剂。该发明还涉及使用这些化合物来抑制细胞生长、诱导细胞死亡、诱导细胞周期停滞和/或使细胞对其他药物敏感。
• SMALL MOLECULE INHIBITORS OF MDM2 AND THE USES THEREOF
  申请人：Wang Shaomeng

  公开号：US20120101092A1

  公开（公告）日：2012-04-26

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  本发明涉及小分子，其作为p53和MDM2相互作用的抑制剂。本发明还涉及使用这些化合物来抑制细胞生长，诱导细胞死亡，诱导细胞周期停滞和/或使细胞对其他药物更敏感。
• PROCESS FOR THE PREPARATION OF SMALL MOLECULE INHIBITORS OF MDM2 AND INTERMEDIATES USED THEREIN
  申请人：Wang Shaomeng

  公开号：US20130030173A1

  公开（公告）日：2013-01-31

  The invention relates to small molecules which function as inhibitors of the interaction between p53 and MDM2. The invention also relates to the use of these compounds for inhibiting cell growth, inducing cell death, inducing cell cycle arrest and/or sensitizing cells to additional agent(s).

  本发明涉及作为p53和MDM2相互作用抑制剂的小分子。本发明还涉及使用这些化合物来抑制细胞生长，诱导细胞死亡，诱导细胞周期阻滞和/或使细胞对其他药物敏感。
• Hybrid molecules of protoflavones and spirooxindole derivatives with selective cytotoxicity against triple-negative breast cancer cells
  作者：Gábor Girst、Elizabeth A. Lopes、Lídia M. Gonçalves、Margarida Espadinha、Norbert Kúsz、Hui-Chun Wang、Maria M. M. Santos、Attila Hunyadi

  DOI：10.1039/d3md00251a

  日期：——

  New lead compounds were synthesized with selectivity against triple negative breast cancer by the combination of DNA damage response inhibitor protoflavones and p53-MDM2/X protein–protein interaction inhibitor spirooxindoles.

  通过 DNA 损伤反应抑制剂原黄酮和 p53-MDM2/X 蛋白-蛋白相互作用抑制剂螺氧化吲哚的组合，合成了对三阴性乳腺癌具有选择性的新先导化合物。
• SMALL MOLECULE INHIBITORS OF MDM2 AND USES THEREOF
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP1856123B1

  公开（公告）日：2016-02-17