N,N'-(1,4-phenylene)bis(4-fluorobenzamide) | 122374-85-0

• 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'-(1,4-phenylene)bis(4-fluorobenzamide)
• 英文别名: 4-fluoro-N-[4-[(4-fluorobenzoyl)amino]phenyl]benzamide
• CAS: 122374-85-0
• 化学式: C₂₀H₁₄F₂N₂O₂
• 分子量: 352.34
• InChiKey: GWGSZVMBTCSBPA-UHFFFAOYSA-N

物化性质

• 沸点：
  380.5±37.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-(1,4-phenylene)bis(4-fluorobenzamide) 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到N,N'-(1,4-phenylene)bis(4-fluorobenzothioamide)
  参考文献：
  名称：

  A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds

  摘要：

  A series of dithiobenzanilide derivatives was synthesized and each compound was evaluated for its ability to reduce KCl-induced contractions of smooth muscle preparations of the guinea pig. Starting from a recent publication describing benzanilide derivatives as antispasmodic agents, structure-activity guided synthesis was performed to obtain compounds with improved spasmolytic activity. First, compounds with two amide bonds were designed and second, both amide oxygens were replaced by two sp(2) sulfur atoms resulting in dithiobenzanilide derivatives. The most potent antispasmodic dithiobenzanilide 19 showed improved activity with an IC50 value of 0.4 mu M. Moreover, the study also demonstrated that these active compounds were able to antagonize the effect of spasmogens like acetylcholine and phenylephrine and that the activity is not mediated by activation of ATP-dependent potassium channels (K-ATP-channels) or inhibition of endothelial nitric oxide synthase (eNOS). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.043
• 作为产物：
  描述：

  对苯二胺 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 N,N'-(1,4-phenylene)bis(4-fluorobenzamide)
  参考文献：
  名称：

  Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation

  摘要：

  Gallic acid (GA), a natural phenolic acid, has received numerous attention because of its anti-oxidative, anti-inflammatory, and anti-cancer activity. More importantly, GA can act as an efficient inhibitor of alpha-Synuclein (alpha-Syn) aggregation at early stages. Nevertheless, some evidences suggest that GA is unlikely to cross the blood-brain barrier because of its high hydrophilicity. Hence, GA may not be considered as a promising candidate or entering brain and directly affecting the central nervous system. Accordingly, we have designed and synthesized a series of amide derivatives of GA, some of which possess appropriate lipophilicity and hydrophilicity with LogP (2.09-2.79). Meanwhile, these sheet-like conjugated compounds have good pi-electron delocalization and high ability of hydrogen-bond formation. Some compounds have shown better in vitro anti-aggregation activities than GA towards alpha-Syn, with IC50, down to 0.98 mu M. The valid modification strategy of GA is considered an efficient way to discover novel inhibitors of alpha-Syn aggregation.

  DOI：

  10.1016/j.bmc.2020.115596