N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide | 6324-67-0

• 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'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide
• 英文别名: N,N'-(3,3'-dimethyl-biphenyl-4,4'-diyl)-bis-benzenesulfonamide；N,N'-(3,3'-Dimethyl-biphenyl-4,4'-diyl)-bis-benzolsulfonamid；N-[4-[4-(benzenesulfonamido)-3-methylphenyl]-2-methylphenyl]benzenesulfonamide
• CAS: 6324-67-0
• 化学式: C₂₆H₂₄N₂O₄S₂
• 分子量: 492.62
• InChiKey: JDIKGJXBVUJVIH-UHFFFAOYSA-N

物化性质

• 熔点：
  251-253 °C
• 沸点：
  648.9±65.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰溴 、 N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(N-(phenylsulfonyl)acetamide)
  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
• 作为产物：
  描述：

  4,4'-二氨基-3,3'-二甲基联苯 、 苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide
  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

• Efficient electrosynthesis of new mono- and bis-sulfonamide derivatives via electrooxidation of o-tolidine
  作者：Saba Parande、Sadegh Khazalpour、Ameneh Amani、Fereshteh Yaghoobi

  DOI：10.1016/j.molstruc.2024.138429

  日期：2024.4

  new mono- and bis-sulfonamide derivatives with o-tolidine (3,3′-dimethylbenzidine) in the central core. Using o-tolidine as a substrate and its electrochemical oxidation as well as the subsequent nucleophilic addition reaction between the oxidized o-tolidine and sulfinic acid derivatives, new mono- and bis-sulfonamide derivatives were synthesized in a solution of acetonitrile/water (30/70 v/v) at pH

  这项工作是第一篇关于合成以邻联苯胺（3,3'-二甲基联苯胺）为中心的新型单磺酰胺和双磺酰胺衍生物的文献。以邻联甲苯胺为底物，通过电化学氧化以及随后氧化的邻联甲苯胺与亚磺酸衍生物之间的亲核加成反应，在乙腈/水(30/ 70 v/v)，pH = 2.0，产率 32–73%。所有合成化合物的化学结构均通过各种分析（包括熔点、IR、1HNMR、13CNMR 和 MS）进行了鉴定和证实。此外，采用 B3LYP/6–311++G(d,p) 理论水平的密度泛函理论 (DFT) 计算，通过福井函数反应性指数分析来研究局部和全局亲电性的化学反应性。 DFT计算得到的结果与实验数据完全一致。
• Quinone Diimides. XV. Diphenoquinonediimides
  作者：Roger Adams、Richard R. Holmes

  DOI：10.1021/ja01132a025

  日期：1952.6
• 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.