4-(4-bromobutoxy)-N-(2-(1H-indol-3-yl)ethyl)benzamide | 1415036-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(4-bromobutoxy)-N-(2-(1H-indol-3-yl)ethyl)benzamide
• CAS: 1415036-73-5
• 化学式: C₂₁H₂₃BrN₂O₂
• 分子量: 415.33
• InChiKey: BIQZJZGQPXMEOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(4-bromobutoxy)-N-(2-(1H-indol-3-yl)ethyl)benzamide 、 4-羟基-二苯甲酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以31%的产率得到4-[4-(4-benzoylphenoxy)butoxy]-N-[2-(1H-indol-3-yl)ethyl]benzamide
  参考文献：
  名称：

  Design, synthesis, and bioevaluation of benzamides: Novel acetylcholinesterase inhibitors with multi-functions on butylcholinesterase, Aβ aggregation, and β-secretase

  摘要：

  Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. In this study, we conducted a structure-based design and successfully produced a series of new multi-site AChE inhibitors with a novel framework. Compound 2e, characterized by a central benzamide moiety linked to an isoquinoline at one side and acetophenone at the other, was the most potent candidate with K-i of 6.47 nM against human AChE. Particularly, it showed simultaneous inhibitory effects against BChE, A beta aggregation, and beta-secretase. We therefore conclude that compound 2e is a very promising multi-function lead for the treatment of AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.016
• 作为产物：
  描述：

  对羟基苯甲酸 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 四氢呋喃 、 丙酮 、 Petroleum ether 为溶剂， 反应 97.0h， 生成 4-(4-bromobutoxy)-N-(2-(1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and bioevaluation of benzamides: Novel acetylcholinesterase inhibitors with multi-functions on butylcholinesterase, Aβ aggregation, and β-secretase

  摘要：

  Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. In this study, we conducted a structure-based design and successfully produced a series of new multi-site AChE inhibitors with a novel framework. Compound 2e, characterized by a central benzamide moiety linked to an isoquinoline at one side and acetophenone at the other, was the most potent candidate with K-i of 6.47 nM against human AChE. Particularly, it showed simultaneous inhibitory effects against BChE, A beta aggregation, and beta-secretase. We therefore conclude that compound 2e is a very promising multi-function lead for the treatment of AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.016