N,N′-[4,4′-methylenebis(4,1-phenylene)]bis(2-bromoacetamide) | 10328-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N′-[4,4′-methylenebis(4,1-phenylene)]bis(2-bromoacetamide)
• 英文别名: N,N'-(methylenedi-4,1-phenylene)bis(2-bromoacetamide)；2-bromo-N-[4-[[4-[(2-bromoacetyl)amino]phenyl]methyl]phenyl]acetamide
• CAS: 10328-56-0
• 化学式: C₁₇H₁₆Br₂N₂O₂
• 分子量: 440.134
• InChiKey: JIGMSVSPBNFLSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N′-[4,4′-methylenebis(4,1-phenylene)]bis(2-bromoacetamide) 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 生成 N,N'-bis[2-(1-pyrrolidinyl)ethyl]-4,4'-diaminodiphenylmethane
  参考文献：
  名称：

  Synthesis of GN8 derivatives and evaluation of their antiprion activity in TSE-infected cells

  摘要：

  A series of GN8 derivatives were synthesized from various diamines, carboxylic acid derivatives, and nitrogen nucleophiles, and their antiprion activity was tested in TSE-infected mouse neuronal cells. We found that two ethylenediamine units, hydrophobic substituents on the nitrogen atoms, and the diphenylmethane scaffold were essential structural features responsible for the activity. Seven derivatives bearing substituents at the benzylic position exhibited an improved antiprion activity with the IC50 values of 0.51-0.83 mu M. Conformational analysis of model compounds suggested that the introduction of the substituent at the benzylic position restricted the conformational variability of the diphenylmethane unit. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.132
• 作为产物：
  描述：

  4,4'-二氨基二苯甲烷 、 溴乙酰溴 在 三乙胺 作用下， 以 氯仿 为溶剂， 以47%的产率得到N,N′-[4,4′-methylenebis(4,1-phenylene)]bis(2-bromoacetamide)
  参考文献：
  名称：

  Bis-carbazole DNA intercalating agents for antitumor therapy

  摘要：

  本发明是一种DNA插入剂，其结构表示为Y-Z-Y，其中Y是一种抗肿瘤双咔唑，Z是多个芳香环的线性排列，含有至少两个芳香环或至少两个脂环，这些环以1,4或1,3方式连接。还提供了使用这些药剂抑制癌细胞和治疗患有癌症的受试者的方法。

  公开号：

  US20100010033A1

文献信息

• Fluorimetric Detection of Insulin Misfolding by Probes Derived from Functionalized Fluorene Frameworks
  作者：Álvaro Sarabia-Vallejo、Ana Molina、Mónica Martínez-Orts、Alice D’Onofrio、Matteo Staderini、Maria Laura Bolognesi、M. Antonia Martín、Ana I. Olives、J. Carlos Menéndez

  DOI：10.3390/molecules29061196

  日期：——

  A group of functionalized fluorene derivatives that are structurally similar to the cellular prion protein ligand N,N′-(methylenedi-4,1-phenylene)bis [2-(1-pyrrolidinyl)acetamide] (GN8) have been synthesized. These compounds show remarkable native fluorescence due to the fluorene ring. The substituents introduced at positions 2 and 7 of the fluorene moiety are sufficiently flexible to accommodate the

  合成了一组结构与细胞朊病毒蛋白配体 N,N'-(亚甲基二-4,1-亚苯基)双[2-(1-吡咯烷基)乙酰胺] (GN8) 结构相似的功能化芴衍生物。由于芴环，这些化合物显示出显着的天然荧光。在芴部分的位置 2 和 7 处引入的取代基足够灵活，可以适应淀粉样蛋白中形成的 β 构象折叠。这些芴衍生物天然荧光的变化提供了胰岛素淀粉样蛋白聚集过程转变的证据。在存在天然胰岛素或淀粉样蛋白聚集体的情况下观察到的传感器荧光强度的增加表明它们有可能用作检测异常构象的荧光探针；因此，这些化合物可以用作“开启”荧光传感器。蛋白质-传感器解离常数在 5-10 μM 范围内，并且可以成功地利用蛋白质和传感器之间的分子间电荷转移过程来灵敏地检测异常胰岛素构象。由于传感器-蛋白质相互作用而获得的化合物 4 的 Stern-Volmer 猝灭常数值与参考化合物 GN8 获得的值相当。芴衍生物在清除活性氧（ROS）方面表现出良好的性能，并且根据
• Synthesis of GN8 derivatives and evaluation of their antiprion activity in TSE-infected cells
  作者：Tsutomu Kimura、Junji Hosokawa-Muto、Yuji O. Kamatari、Kazuo Kuwata

  DOI：10.1016/j.bmcl.2010.12.132

  日期：2011.3

  A series of GN8 derivatives were synthesized from various diamines, carboxylic acid derivatives, and nitrogen nucleophiles, and their antiprion activity was tested in TSE-infected mouse neuronal cells. We found that two ethylenediamine units, hydrophobic substituents on the nitrogen atoms, and the diphenylmethane scaffold were essential structural features responsible for the activity. Seven derivatives bearing substituents at the benzylic position exhibited an improved antiprion activity with the IC50 values of 0.51-0.83 mu M. Conformational analysis of model compounds suggested that the introduction of the substituent at the benzylic position restricted the conformational variability of the diphenylmethane unit. (C) 2011 Elsevier Ltd. All rights reserved.
• Bis-carbazole DNA intercalating agents for antitumor therapy
  申请人：Gribble Gordon W.

  公开号：US20100010033A1

  公开（公告）日：2010-01-14

  The present invention is a DNA intercalating agent represented by the structure Y-Z-Y, wherein Y is an anti-tumor bis-carbazole and Z is a linear arrangement of multiple aromatic rings, containing at least two aromatic rings, or at least two alicyclic rings, said rings being linked in a 1,4 or 1,3 manner. Methods of inhibiting cancer cells and treating subjects having cancer with these agents are also provided.

  本发明是一种DNA插入剂，其结构表示为Y-Z-Y，其中Y是一种抗肿瘤双咔唑，Z是多个芳香环的线性排列，含有至少两个芳香环或至少两个脂环，这些环以1,4或1,3方式连接。还提供了使用这些药剂抑制癌细胞和治疗患有癌症的受试者的方法。