2-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]-N,N-diethylethanamine | 17926-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]-N,N-diethylethanamine
• 英文别名: 2-(4-(1H-benzo[d]imidazol-2-yl)phenoxy)-N,N-diethylethan-1-amine；{2-[4-(1H-benzoimidazol-2-yl)-phenoxy]-ethyl}-diethyl-amine；2-[4-(1H-benzimidazol-2-yl)phenoxy]-N,N-diethylethanamine
• CAS: 17926-03-3
• 化学式: C₁₉H₂₃N₃O
• 分子量: 309.411
• InChiKey: YOVHNJSQWZOPJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 2-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]-N,N-diethylethanamine 以 1,2-二氯乙烷 为溶剂， 以50 %的产率得到2-(4-(1H-benzo[d]imidazol-2-yl)phenoxy)-N,N,N-triethylethan-1-aminium iodide
  参考文献：
  名称：

  Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c01256
• 作为产物：
  描述：

  sodium hydroxy(4-hydroxyphenyl)methanesulfonate 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]-N,N-diethylethanamine
  参考文献：
  名称：

  Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors

  摘要：

  A series of N-(2-[4-(1H-benzimidazole-2-yl)phenoxy]ethyl}substituted amine derivatives were designed to assess cholinesterase inhibitor activities. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitor activities were evaluated in vitro by using Ellman's method. It was discovered that most of the compounds displayed AChE and/or BuChE inhibitor activity and few compounds were selective against AChE/BuChE. Compound 3c and 3e were the most active compounds in the series against eeAChE and hAChE, respectively. Molecular docking studies and molecular dynamics simulations were also carried out. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.065

文献信息

• Synthesis, biological activity and molecular modeling studies on 1H-benzimidazole derivatives as acetylcholinesterase inhibitors
  作者：Ayşe Selcen Alpan、Sülünay Parlar、Luca Carlino、Ayse Hande Tarikogullari、Vildan Alptüzün、Hasan Semih Güneş

  DOI：10.1016/j.bmc.2013.06.065

  日期：2013.9

  A series of N-(2-[4-(1H-benzimidazole-2-yl)phenoxy]ethyl}substituted amine derivatives were designed to assess cholinesterase inhibitor activities. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitor activities were evaluated in vitro by using Ellman's method. It was discovered that most of the compounds displayed AChE and/or BuChE inhibitor activity and few compounds were selective against AChE/BuChE. Compound 3c and 3e were the most active compounds in the series against eeAChE and hAChE, respectively. Molecular docking studies and molecular dynamics simulations were also carried out. (C) 2013 Elsevier Ltd. All rights reserved.
• Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)
  作者：Francesco Bavo、Marco Pallavicini、Susanna Pucci、Rebecca Appiani、Alessandro Giraudo、Hyoungil Oh、Dana L. Kneisley、Brek Eaton、Linda Lucero、Cecilia Gotti、Francesco Clementi、Paul Whiteaker、Cristiano Bolchi

  DOI：10.1021/acs.jmedchem.2c01256

  日期：2023.1.12