4-(4-Chloro-3-hydroxyphenyl)but-3-en-2-one

• 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: 4-(4-Chloro-3-hydroxyphenyl)but-3-en-2-one
• 英文别名: 4-(4-chloro-3-hydroxyphenyl)but-3-en-2-one
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: VEVWSLXHTMAROA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-Chloro-3-hydroxyphenyl)but-3-en-2-one 在 2-pyrrolidinone hydrotribromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 3-O-[(E)-4-(3-hydroxy-4-chlorophenyl)-2-oxobut-3-en-1-yl]kaempferol
  参考文献：
  名称：

  Synthesis and biological activity of novel tiliroside derivants

  摘要：

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.059
• 作为产物：
  描述：

  4-氯-3-羟基苯甲醛 、 丙酮 在 sodium hydroxide 作用下， 生成 4-(4-Chloro-3-hydroxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Synthesis and biological activity of novel tiliroside derivants

  摘要：

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.059

文献信息

• Synthesis and biological activity of novel tiliroside derivants
  作者：Nan Qin、Chun-Bao Li、Mei-Na Jin、Li-Huan Shi、Hong-Quan Duan、Wen-Yan Niu

  DOI：10.1016/j.ejmech.2011.07.059

  日期：2011.10

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.