(E)-3-(thiophen-3-yl)prop-2-ynyl 2-cyano-3-(3,4-dihydroxyphenyl)acrylate | 1579956-00-5

• 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-(thiophen-3-yl)prop-2-ynyl 2-cyano-3-(3,4-dihydroxyphenyl)acrylate
• 英文别名: 3-thiophen-3-ylprop-2-ynyl (E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 1579956-00-5
• 化学式: C₁₇H₁₁NO₄S
• 分子量: 325.345
• InChiKey: RWOZRIGASHDKIW-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(3-噻吩基)-2-丙炔-1-醇 在 哌啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(thiophen-3-yl)prop-2-ynyl 2-cyano-3-(3,4-dihydroxyphenyl)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

文献信息

• PAIN RELIEF COMPOUNDS
  申请人：ECOLE NATIONALE SUPERIEURE DE CHIMIE DE CLERMONT FERRAND

  公开号：US20150274633A2

  公开（公告）日：2015-10-01

  The present invention relates to the use of compounds for the treatment or prevention of pain in mammals, in particularly in human beings, and also to a process for preparing these compounds.

  本发明涉及使用化合物治疗或预防哺乳动物（尤其是人类）的疼痛，以及制备这些化合物的方法。
• [EN] PAIN RELIEF COMPOUNDS<br/>[FR] COMPOSES ANTI-DOULEUR
  申请人：ECOLE NALE SUP ARTES METIERS

  公开号：WO2013098416A2

  公开（公告）日：2013-07-04

  La présente invention concerne l'utilisation de composés pour le traitement ou la prévention de la douleur chez le mammifère, notamment chez l'homme, ainsi qu'un procédé de préparation de ces composés.