ethyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate | 1579955-85-3

• 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: ethyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate
• CAS: 1579955-85-3
• 化学式: C₂₁H₃₁NO₈
• 分子量: 425.479
• InChiKey: CILLJYDFWZIVSS-YBEGLDIGSA-N

物化性质

• 沸点：
  556.6±50.0 °C(predicted)
• 密度：
  1.144±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 18.0h， 生成 ethyl 3-(3,4-bis(methoxymethoxy)phenyl)-2-((tert-butoxycarbonylamino)methyl)acrylate 、 ethyl 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