(3E,5E)-3-(3,4,5-trimethoxybenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E,5E)-3-(3,4,5-trimethoxybenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-3-[(3,5-dimethoxyphenyl)methylidene]-1-methyl-5-[(3,4,5-trimethoxyphenyl)methylidene]piperidin-4-one
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: AEUZHOHJVCCDKO-NDILIQOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 3,5-二甲氧基苯甲醛 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以43%的产率得到(3E,5E)-3-(3,4,5-trimethoxybenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Novel dissymmetric 3,5-bis(arylidene)-4-piperidones as potential antitumor agents with biological evaluation in vitro and in vivo

  摘要：

  Thirty-five novel dissymmetric 3,5-bis(arylidene)-4-piperidone derivatives (BAPS, 6a-h, 7a-h, 8a-g, 9a-g, 10a-e) were synthesized and evaluated the cytotoxicity. BAPS 6d, 7h, 8g, 9g demonstrated the most potentially inhibitory activities against HepG2 and THP-1 but lower cytotoxicity toward LO2. In vitro, 6d, 7h, 8g, 9g can effectively up-regulate BAX expression, down-regulate Bcl-2 expression in HepG2 cell. They could reasonably bind to the active site of Bcl-2 protein proved by molecular docking modes. The most active BAP 6d induced HepG2 cells apoptosis in a dose-dependent manner by flow cytometrey. The cellular uptake of HepG2 cells showed 6d mainly accumulated into the nuclei by confocal laser scanning microscopy (CLSM). In vivo, 6d suppressed the growth of HepG2 xenografts in nude mice and relatively nontoxic to mice. These results suggest that 6d could be therapeutically beneficial as potential therapeutic agent for the early clinical treatment of liver cancers. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.088

文献信息

• Novel dissymmetric 3,5-bis(arylidene)-4-piperidones as potential antitumor agents with biological evaluation in vitro and in vivo
  作者：Ning Li、Wen-Yu Xin、Bin-Rong Yao、Chun-Hua Wang、Wei Cong、Feng Zhao、Hong-Juan Li、Yun Hou、Qing-Guo Meng、Gui-Ge Hou

  DOI：10.1016/j.ejmech.2018.01.088

  日期：2018.3

  Thirty-five novel dissymmetric 3,5-bis(arylidene)-4-piperidone derivatives (BAPS, 6a-h, 7a-h, 8a-g, 9a-g, 10a-e) were synthesized and evaluated the cytotoxicity. BAPS 6d, 7h, 8g, 9g demonstrated the most potentially inhibitory activities against HepG2 and THP-1 but lower cytotoxicity toward LO2. In vitro, 6d, 7h, 8g, 9g can effectively up-regulate BAX expression, down-regulate Bcl-2 expression in HepG2 cell. They could reasonably bind to the active site of Bcl-2 protein proved by molecular docking modes. The most active BAP 6d induced HepG2 cells apoptosis in a dose-dependent manner by flow cytometrey. The cellular uptake of HepG2 cells showed 6d mainly accumulated into the nuclei by confocal laser scanning microscopy (CLSM). In vivo, 6d suppressed the growth of HepG2 xenografts in nude mice and relatively nontoxic to mice. These results suggest that 6d could be therapeutically beneficial as potential therapeutic agent for the early clinical treatment of liver cancers. (C) 2018 Elsevier Masson SAS. All rights reserved.