N-{[2-(Benzyloxy)phenyl]methylene}-N-(4-methylphenyl)amine | 634594-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-{[2-(Benzyloxy)phenyl]methylene}-N-(4-methylphenyl)amine
• 英文别名: N-(4-methylphenyl)-1-(2-phenylmethoxyphenyl)methanimine
• CAS: 634594-65-3
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: LRESEYSYBUYARF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-naphthaldehyde tosylhydrazone 、 N-{[2-(Benzyloxy)phenyl]methylene}-N-(4-methylphenyl)amine 在 亚碘酰苯 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(4-methylphenyl)-2-(4-methylphenyl)sulfonyl-5-naphthalen-2-yl-3-(2-phenylmethoxyphenyl)-3H-1,2,4-triazole
  参考文献：
  名称：

  Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: reaction, scope, and synthesis

  摘要：

  生成了偶氮亚胺及其在亚胺与PhIO的区域选择性1,3-偶极环加成（DC）中的应用，形成高度取代的Δ2-1,2,4-三唑啉、1,2,4-三唑及其融合、手性和基于糖的类似物。

  DOI：

  10.1039/b924761k
• 作为产物：
  描述：

  乙烷,三氯氟- 、 2-苄氧基苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-{[2-(Benzyloxy)phenyl]methylene}-N-(4-methylphenyl)amine
  参考文献：
  名称：

  Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: reaction, scope, and synthesis

  摘要：

  生成了偶氮亚胺及其在亚胺与PhIO的区域选择性1,3-偶极环加成（DC）中的应用，形成高度取代的Δ2-1,2,4-三唑啉、1,2,4-三唑及其融合、手性和基于糖的类似物。

  DOI：

  10.1039/b924761k

文献信息

• Identification of small molecule sphingomyelin synthase inhibitors
  作者：Xiaodong Deng、Fu Lin、Ya Zhang、Yan Li、Lu Zhou、Bin Lou、Yue Li、Jibin Dong、Tingbo Ding、Xiancheng Jiang、Renxiao Wang、Deyong Ye

  DOI：10.1016/j.ejmech.2013.12.002

  日期：2014.2

  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.
• Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: reaction, scope, and synthesis
  作者：Dilip K. Maiti、Nirbhik Chatterjee、Palash Pandit、Sandip K. Hota

  DOI：10.1039/b924761k

  日期：——

  Generation of azomethine imine and its scope in regioselective 1,3-dipolar cycloaddition (DC) of imine with PhIO toward highly substituted Δ2-1,2,4-triazoline, 1,2,4-triazole, and their fused, chiral, and sugar-based analogues are demonstrated.

  生成了偶氮亚胺及其在亚胺与PhIO的区域选择性1,3-偶极环加成（DC）中的应用，形成高度取代的Δ2-1,2,4-三唑啉、1,2,4-三唑及其融合、手性和基于糖的类似物。