2-(3-chloro-5-methoxy-benzylsulfanyl)-ethylamine | 1147093-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-chloro-5-methoxy-benzylsulfanyl)-ethylamine
• 英文别名: 2-(3-Chloro-5-methoxy-benzylsulfanyl)-ethylamine；2-[(3-chloro-5-methoxyphenyl)methylsulfanyl]ethanamine
• CAS: 1147093-48-8
• 化学式: C₁₀H₁₄ClNOS
• 分子量: 231.746
• InChiKey: ZDMDMWNAWLGAPG-UHFFFAOYSA-N

物化性质

• 沸点：
  344.7±37.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-chloro-5-methoxy-benzylsulfanyl)-ethylamine 、 2,6-二氯苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-dichloro-N-[2-(3-chloro-5-methoxy-benzylsulfanyl)-ethyl]-benzamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of a Novel Inhibitor of β-Amyloid Secretion

  摘要：

  A drug library of 17200 compounds was screened to select small molecules that inhibit the secretion of amyloid beta peptide (Am, the major component of Alzheimer disease senile plaques, from a human neuronal cell line. Twenty-nine hits were validated that decreased A beta secretion by >40% at 10 mu M, for a 0.17% hit rate. A lead hit was selected for further study based on its activity and low cytotoxicity, and it was found to inhibit A beta secretion through activation of the alpha-secretase pathway. Twenty-four commercially available and 53 synthesized analogues were analyzed for activity. Selected analogues were evaluated for biological stability by incubation with hepatoma cells and for transcellular permeability using Caco-2 cell monolayers. The analogue with the best permeability was evaluated in 2-month old amyloid precursor protein transgenic mice and found to acutely reduce cerebral A beta levels by 40% after a single iv administration.

  DOI：

  10.1021/jm100308g
• 作为产物：
  描述：

  半胱胺盐酸盐 、 3-氯-5-甲氧基苄氯 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 以78%的产率得到2-(3-chloro-5-methoxy-benzylsulfanyl)-ethylamine
  参考文献：
  名称：

  A new strategy for the synthesis of β-benzylmercaptoethylamine derivatives

  摘要：

  Here, we describe a new experimental approach to the synthesis of the beta-benzylmercaptoethylamine functionality, and illustrate its synthetic utility in multi-component reactions. Although prevalent in modern organic synthesis, no general methods have been described for this functionality. Using a carefully developed LiOH-water-ethanol reaction mixture, we were able to produce a diverse collection of beta-benzylmercaptoethylamines containing a range of sensitive functional groups in excellent yields. To further illustrate their utility in molecular library synthesis, we also report the use of beta-benzylmercaptoethylamines in five different multi-component reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.133