N,N'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis(2-bromoacetamide) | 1255768-08-1

• 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'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis(2-bromoacetamide)
• 英文别名: 2-bromo-N-[4-[1-[4-[(2-bromoacetyl)amino]phenyl]-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]phenyl]acetamide
• CAS: 1255768-08-1
• 化学式: C₂₄H₁₈Br₂F₄N₂O₂
• 分子量: 602.221
• InChiKey: BVWOTGHQNQPVBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 N,N'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis(2-bromoacetamide) 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95 mg的产率得到N,N'-[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene-di-4,1-phenylene]bis[2-(1-pyrrolidinyl)acetamide]
  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：

  苯胺 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 N,N'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis(2-bromoacetamide)
  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