(E)-ethyl 3-(3,5-dimethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate | 1345729-02-3

• 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)-ethyl 3-(3,5-dimethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate
• 英文别名: ethyl (E)-3-[3,5-dimethoxy-4-[(3,5,6-trimethylpyrazin-2-yl)methoxy]phenyl]prop-2-enoate
• CAS: 1345729-02-3
• 化学式: C₂₁H₂₆N₂O₅
• 分子量: 386.448
• InChiKey: HETLKKVISALXOV-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(3,5-dimethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以87%的产率得到(E)-3-(3,5-dimethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylic acid
  参考文献：
  名称：

  Ligustrazine derivatives. Part 5: Design, synthesis and biological evaluation of novel ligustrazinyloxy-cinnamic acid derivatives as potent cardiovascular agents

  摘要：

  A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H2O2)-induced oxidative damage on ECV-304 cells. Some compounds exhibited high activity in one or both of the assays, of which, compound 2e displayed the highest protective effect on the proliferation of the damaged ECV-304 cells (EC50=0.020 mM), and compound 2f was the most active anti-platelet aggregation agent (EC50=0.054 mM). Structure activity relationships were briefly discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.030
• 作为产物：
  描述：

  2-chloromethyl-3,5,6-trimethyl-pyrazine hydrochloride 、 ethyl sinapate 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (E)-ethyl 3-(3,5-dimethoxy-4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate
  参考文献：
  名称：

  Ligustrazine derivatives. Part 5: Design, synthesis and biological evaluation of novel ligustrazinyloxy-cinnamic acid derivatives as potent cardiovascular agents

  摘要：

  A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H2O2)-induced oxidative damage on ECV-304 cells. Some compounds exhibited high activity in one or both of the assays, of which, compound 2e displayed the highest protective effect on the proliferation of the damaged ECV-304 cells (EC50=0.020 mM), and compound 2f was the most active anti-platelet aggregation agent (EC50=0.054 mM). Structure activity relationships were briefly discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.030

文献信息

• Ligustrazine derivatives. Part 5: Design, synthesis and biological evaluation of novel ligustrazinyloxy-cinnamic acid derivatives as potent cardiovascular agents
  作者：Hongfei Chen、Guoning Li、Peng Zhan、Xinyong Liu

  DOI：10.1016/j.ejmech.2011.09.030

  日期：2011.11

  A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H2O2)-induced oxidative damage on ECV-304 cells. Some compounds exhibited high activity in one or both of the assays, of which, compound 2e displayed the highest protective effect on the proliferation of the damaged ECV-304 cells (EC50=0.020 mM), and compound 2f was the most active anti-platelet aggregation agent (EC50=0.054 mM). Structure activity relationships were briefly discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.