(E)-3-(benzo[d][1,3]dioxol-5-yl)-N-(2-hydroxyethyl)acrylamide | 1187423-40-0

• 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-(benzo[d][1,3]dioxol-5-yl)-N-(2-hydroxyethyl)acrylamide
• 英文别名: (E)-3-(1,3-benzodioxol-5-yl)-N-(2-hydroxyethyl)prop-2-enamide
• CAS: 1187423-40-0
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD12415588
• 分子量: 235.24
• InChiKey: VIAUAKJPQDDTGA-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C.I.酸性橙108 、 3,4-(亚甲二氧)肉桂酸 在 三乙胺 、 氯甲酸甲酯 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(E)-3-(benzo[d][1,3]dioxol-5-yl)-N-(2-hydroxyethyl)acrylamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of N-(2-hydroxyethyl) cinnamamide derivatives

  摘要：

  A series of novel N-(2-hydroxyethyl) cinnamamide derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The MES test showed that compounds l(N-(2-hydroxyethyl) cinnamamide) and 1d ((E)-3-(3-fluorophenyl)-N-(2-hydroxyethyl)acrylamide) were found to possess better anticonvulsant activity but also had lower toxicity. In the anti-MES potency test, these compounds exhibited median effective dose (ED50) of 17.7 and 17.0 mg/kg, respectively, and median toxicity dose (TD50) of 154.9 and 211.1, respectively, resulting in a protective index (PI) of 8.8 and 12.4, respectively, which is much greater than the PI of the marked antiepileptic drug carbamazepine. To further investigate the effects of the anticonvulsant activity in several different models, compounds I and 1d were tested against convulsions induced by chemical substances, including pentylenetetrazole (PTZ), isoniazid, 3-mercaptopropionic acid, and thiosemicarbazide. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.015

文献信息

• Synthesis and anticonvulsant activity of N-(2-hydroxyethyl) cinnamamide derivatives
  作者：Li-Ping Guan、Cheng-Xi Wei、Xian-Qing Deng、Xin Sui、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2009.02.015

  日期：2009.9

  A series of novel N-(2-hydroxyethyl) cinnamamide derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The MES test showed that compounds l(N-(2-hydroxyethyl) cinnamamide) and 1d ((E)-3-(3-fluorophenyl)-N-(2-hydroxyethyl)acrylamide) were found to possess better anticonvulsant activity but also had lower toxicity. In the anti-MES potency test, these compounds exhibited median effective dose (ED50) of 17.7 and 17.0 mg/kg, respectively, and median toxicity dose (TD50) of 154.9 and 211.1, respectively, resulting in a protective index (PI) of 8.8 and 12.4, respectively, which is much greater than the PI of the marked antiepileptic drug carbamazepine. To further investigate the effects of the anticonvulsant activity in several different models, compounds I and 1d were tested against convulsions induced by chemical substances, including pentylenetetrazole (PTZ), isoniazid, 3-mercaptopropionic acid, and thiosemicarbazide. (C) 2009 Elsevier Masson SAS. All rights reserved.