2-(2-(benzyloxy)phenyl)-2-((4 methoxyphenyl) amino)acetonitrile | 573972-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(benzyloxy)phenyl)-2-((4 methoxyphenyl) amino)acetonitrile
• 英文别名: [2-(Benzyloxy)phenyl][(4-methoxyphenyl)amino]acetonitrile；2-(4-methoxyanilino)-2-(2-phenylmethoxyphenyl)acetonitrile
• CAS: 573972-10-8
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: ZJAGOXOQBYLFBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  543.5±50.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 N-[(1E/Z)-[2-(benzyloxy)phenyl]methylene]-4-methoxyaniline 在 碘 作用下， 以263 mg的产率得到2-(2-(benzyloxy)phenyl)-2-((4 methoxyphenyl) amino)acetonitrile
  参考文献：
  名称：

  Identification of small molecule sphingomyelin synthase inhibitors

  摘要：

  Sphingomyelin synthase (SMS), which catalyzes ceramide as one of the substrates to produce sphingomyelin, is a critical factor in the sphingolipid biosynthesis pathway. Recent studies indicated that SMS could serve as a novel potential drug target for the treatment of various metabolic diseases such as insulin resistance and atherosclerosis. However, very few small-molecule inhibitors of SMS are known. In this study, we performed structure-based virtual screening in combination with chemical synthesis and bioassay and discovered a class of small-molecule SMS inhibitors. The most potent compound exhibited an IC50 value lower than 20 mu M in an in vitro enzymatic assay. To the best of our knowledge, this is the first time that small-molecule SMS inhibitors with potency close to the micromolar range are publicly revealed. The structure-activity relationship demonstrated by this class of compounds provides insights into the structural features that are essential for effective SMS inhibition. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.002