(E)-cinnamyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate | 1579956-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-cinnamyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate
• CAS: 1579956-07-2
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: LRMPJICPAGGSQL-FTFFFJSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-cinnamyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以40%的产率得到(E)-2-(cinnamyloxycarbonyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-ammonium chloride
  参考文献：
  名称：

  Synthesis and structure–activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel

  摘要：

  The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs. It has been reported that TREK-1 -/- mice were more sensitive than wild-type mice to painful stimuli, suggesting that activation of TREK-1 could result in pain inhibition. Here we report the synthesis of a series of substituted caffeate esters (12a-u) based on the hit compound CDC 2 (cinnamyl 3,4-dihydroxyl-alpha-cyanocinnamate). These analogs were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid induced-writhing assay) leading to the identification a series of novel molecules able to activate TREK-1 and displaying potent analgesic activity in vivo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.049
• 作为产物：
  描述：

  ethyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (E)-cinnamyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate
  参考文献：
  名称：

  Synthesis and structure–activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel

  摘要：

  The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs. It has been reported that TREK-1 -/- mice were more sensitive than wild-type mice to painful stimuli, suggesting that activation of TREK-1 could result in pain inhibition. Here we report the synthesis of a series of substituted caffeate esters (12a-u) based on the hit compound CDC 2 (cinnamyl 3,4-dihydroxyl-alpha-cyanocinnamate). These analogs were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid induced-writhing assay) leading to the identification a series of novel molecules able to activate TREK-1 and displaying potent analgesic activity in vivo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.049