5-(4'-hydroxy-3'-methoxy-phenyl)-2E-propenoic acid thiomorpholine amide | 1228296-73-8

• 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: 5-(4'-hydroxy-3'-methoxy-phenyl)-2E-propenoic acid thiomorpholine amide
• 英文别名: (E)-3-(4-hydroxy-3-methoxyphenyl)-1-thiomorpholin-4-ylprop-2-en-1-one
• CAS: 1228296-73-8
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: NEXAVEHOUSBMGM-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硫代吗啉 、 阿魏酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到5-(4'-hydroxy-3'-methoxy-phenyl)-2E-propenoic acid thiomorpholine amide
  参考文献：
  名称：

  In vitro TRPV1 activity of piperine derived amides

  摘要：

  A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.013

文献信息

• In vitro TRPV1 activity of piperine derived amides
  作者：Edwin Andrés Correa、Edward D. Högestätt、Olov Sterner、Fernando Echeverri、Peter M. Zygmunt

  DOI：10.1016/j.bmc.2010.03.013

  日期：2010.5

  A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity. (C) 2010 Elsevier Ltd. All rights reserved.