N-(2-羟基乙基)-3-(4-甲氧基苯基)丙-2-烯酰胺 | 30687-06-0

• 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
• 中文名称: N-(2-羟基乙基)-3-(4-甲氧基苯基)丙-2-烯酰胺
• 英文名称: (E)-N-(2-hydroxyethyl)-3-(4-methoxyphenyl)acrylamide
• 英文别名: Cinnamamide, N-(2-hydroxyethyl)-4-methoxy-；(E)-N-(2-hydroxyethyl)-3-(4-methoxyphenyl)prop-2-enamide
• CAS: 30687-06-0
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD01736631
• 分子量: 221.256
• InChiKey: RMWDGIYZUHYPPL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2-羟基乙基)-3-(4-甲氧基苯基)丙-2-烯酰胺 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以53.1%的产率得到(E)-N-(2-hydroxyethyl)-3-(4-hydroxyphenyl)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
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(2-羟基乙基)-3-(4-甲氧基苯基)丙-2-烯酰胺
  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
• NOVEL FLAVORS, FLAVOR MODIFIERS, TASTANTS, TASTE ENHANCERS, UMAMI OR SWEET TASTANTS, AND/OR ENHANCERS AND USE THEREOF
  申请人：Senomyx Inc.

  公开号：EP1659881B1

  公开（公告）日：2019-04-03
• 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.