(E)-3-(3,4-dimethoxyphenyl)-N-(2-hydroxyethyl)acrylamide | 30687-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-dimethoxyphenyl)-N-(2-hydroxyethyl)acrylamide
• 英文别名: 3,4-Dimethoxy-N-(2-hydroxyethyl)cinnamamide；(E)-3-(3,4-dimethoxyphenyl)-N-(2-hydroxyethyl)prop-2-enamide
• CAS: 30687-22-0
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: BPZBBNACOBZIRU-GQCTYLIASA-N

物化性质

• 沸点：
  503.9±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)-N-(2-hydroxyethyl)acrylamide 、 双氢青蒿素 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以49%的产率得到
  参考文献：
  名称：

  Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104903
• 作为产物：
  描述：

  C.I.酸性橙108 、 以 二氯甲烷 为溶剂， 生成 (E)-3-(3,4-dimethoxyphenyl)-N-(2-hydroxyethyl)acrylamide
  参考文献：
  名称：

  Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice

  摘要：

  This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, (1)H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.

  DOI：

  10.1007/s00044-010-9470-7

文献信息

• Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway
  作者：Yanping Hu、Yujin Wang、Na Li、Li Chen、Jianbo Sun

  DOI：10.1016/j.bioorg.2021.104903

  日期：2021.6
• Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice
  作者：Xian-Qing Deng、Di Wu、Cheng-Xi Wei、Zhe-Shan Quan

  DOI：10.1007/s00044-010-9470-7

  日期：2011.11

  This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, (1)H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.