N,N'-(biphenyl-4,4'-diyl)bis(N-butylbenzenesulfonamide)

• 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'-(biphenyl-4,4'-diyl)bis(N-butylbenzenesulfonamide)
• 英文别名: N,N'-(biphenyl-4,4'-diyl)bis(N-butylbenzenesulfonamide) (3c)；N-[4-[4-[benzenesulfonyl(butyl)amino]phenyl]phenyl]-N-butylbenzenesulfonamide
• 化学式: C₃₂H₃₆N₂O₄S₂
• 分子量: 576.781
• InChiKey: CDSDOJIDVBWMJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  联苯胺 在 吡啶 、 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N,N'-(biphenyl-4,4'-diyl)bis(N-butylbenzenesulfonamide)
  参考文献：
  名称：

  Novel biphenyl bis -sulfonamides as acetyl and butyrylcholinesterase inhibitors: Synthesis, biological evaluation and molecular modeling studies

  摘要：

  A series of new biphenyl bis-sulfonamide derivatives 2a-3p were synthesized in good to excellent yield (76-98%). The inhibitory potential of the synthesized compounds on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) was investigated. Most of the screened compounds showed modest in vitro inhibition for both AChE and BChE. Compared to the reference compound eserine (IC50 0.04 +/- 0.0001 mu M for AChE) and (IC50 0.85 +/- 0.0001 mu M for BChE), the IC50 values of these compounds were ranged from 2.27 +/- 0.01 to 123.11 +/- 0.04 mu M for AChE and 7.74 +/- 0.07 to < 400 mu M for BuChE. Among the tested compounds, 3p was found to be the most potent against AChE (IC50 2.27 +/- 0.01 mu M), whereas 3g exhibited the highest inhibition for BChE (IC50 7.74 +/- 0.07 mu M). Structure-activity relationship (SAR) of these compounds was developed and elaborated with the help of molecular docking studies. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.11.002

文献信息

• Novel biphenyl bis -sulfonamides as acetyl and butyrylcholinesterase inhibitors: Synthesis, biological evaluation and molecular modeling studies
  作者：Sadaf Mutahir、Jakub Jończyk、Marek Bajda、Islam Ullah Khan、Muhammad Asim Khan、Nisar Ullah、Muhammad Ashraf、Qurat-ul-Ain、Sadaf Riaz、Sajjad Hussain、Muhammad Yar

  DOI：10.1016/j.bioorg.2015.11.002

  日期：2016.2

  A series of new biphenyl bis-sulfonamide derivatives 2a-3p were synthesized in good to excellent yield (76-98%). The inhibitory potential of the synthesized compounds on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) was investigated. Most of the screened compounds showed modest in vitro inhibition for both AChE and BChE. Compared to the reference compound eserine (IC50 0.04 +/- 0.0001 mu M for AChE) and (IC50 0.85 +/- 0.0001 mu M for BChE), the IC50 values of these compounds were ranged from 2.27 +/- 0.01 to 123.11 +/- 0.04 mu M for AChE and 7.74 +/- 0.07 to < 400 mu M for BuChE. Among the tested compounds, 3p was found to be the most potent against AChE (IC50 2.27 +/- 0.01 mu M), whereas 3g exhibited the highest inhibition for BChE (IC50 7.74 +/- 0.07 mu M). Structure-activity relationship (SAR) of these compounds was developed and elaborated with the help of molecular docking studies. (C) 2015 Elsevier Inc. All rights reserved.