(1E,6E)-1,7-bis[4-(trifluoromethyl)phenyl]hepta-1,6-diene-3,5-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,6E)-1,7-bis[4-(trifluoromethyl)phenyl]hepta-1,6-diene-3,5-dione
• 化学式: C₂₁H₁₄F₆O₂
• 分子量: 412.331
• InChiKey: GJGHGKMVJJXPQE-YDWXAUTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 乙酰丙酮 在 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以51%的产率得到(1E,6E)-1,7-bis[4-(trifluoromethyl)phenyl]hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  3,3′-OH curcumin causes apoptosis in HepG2 cells through ROS-mediated pathway

  摘要：

  In this paper, we synthesized a series of curcumin analogs and evaluated their cytotoxicity against HepG2 cells. The results exhibited that the hydroxyl group at 3,3'-position play an essential role in enhancing their anti-proliferation activity. More importantly, 3,3'-hydroxy curcumin (1b) caused apoptosis in HepG2 cells with the ROS generation, which may be mainly composed of hydroxyl radicals (HO center dot) and H2O2. The more cytotoxic activity and ROS-generating ability of 1b may be due to the more stable in (RPMI)-1640 medium and more massive uptake than curcumin. Then the generation of ROS can disrupt the intracellular redox balance, induce lipid peroxidation, cause the collapse of the mitochondrial membrane potential and ultimately lead to apoptosis. The results not only suggest that 3,3'-hydroxy curcumin (1b) may cause HepG2 cells apoptosis through ROS-mediated pathway, but also offer an important information for design of curcumin analog. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.019