N,N'-(1,4-phenylene)bis(3,4,5-trimethoxybenzothioamide) | 1270966-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N'-(1,4-phenylene)bis(3,4,5-trimethoxybenzothioamide)
• 英文别名: 3,4,5-trimethoxy-N-[4-[(3,4,5-trimethoxybenzenecarbothioyl)amino]phenyl]benzenecarbothioamide
• CAS: 1270966-02-3
• 化学式: C₂₆H₂₈N₂O₆S₂
• 分子量: 528.65
• InChiKey: SCIPTKVHFNMWSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N,N'-(1,4-phenylene)bis(3,4,5-trimethoxybenzamide) 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以77.7%的产率得到N,N'-(1,4-phenylene)bis(3,4,5-trimethoxybenzothioamide)
  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

文献信息

• A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds
  作者：Gerda Brunhofer、Walter H. Granig、Christian R. Studenik、Thomas Erker

  DOI：10.1016/j.bmc.2010.11.043

  日期：2011.1

  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.