N-((8-hydroxy-1,3-dimethoxy-9,10-anthraquinone-6-yl)methyl)-N,N-dimethyloctan-1-aminium bromide | 1413289-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-((8-hydroxy-1,3-dimethoxy-9,10-anthraquinone-6-yl)methyl)-N,N-dimethyloctan-1-aminium bromide
• 英文别名: (4-Hydroxy-5,7-dimethoxy-9,10-dioxoanthracen-2-yl)methyl-dimethyl-octylazanium;bromide；(4-hydroxy-5,7-dimethoxy-9,10-dioxoanthracen-2-yl)methyl-dimethyl-octylazanium;bromide
• CAS: 1413289-91-4
• 化学式: Br*C₂₇H₃₆NO₅
• 分子量: 534.491
• InChiKey: KDXXYLUBYLGTDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N-二甲基正辛胺 、 6-Bromomethyl-1,3,8-trimethoxy-6-methyl-anthraquinone 在 氢溴酸 作用下， 以 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 N-((8-hydroxy-1,3-dimethoxy-9,10-anthraquinone-6-yl)methyl)-N,N-dimethyloctan-1-aminium bromide 、 N-((1-hydroxy-3,8-dimethoxy-9,10-anthraquinone-6-yl)methyl)-N,N-dimethyloctan-1-aminium bromide
  参考文献：
  名称：

  Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents

  摘要：

  Twenty-six emodin derivatives (17 novel) which attach quaternary ammonium salt were synthesized and evaluated for their anticancer activities in vitro and in vivo. Compounds 11g + 12g and 11h + 12h had more significant antiproliferative ability against three cancer cell lines and low cytotoxicity to HELF. 11g + 12g and 11 h + 12h induced AGS cell apoptosis and arrested cell cycle at the G(0)/G(1) phase in a dose-dependent manner. Furthermore, the activities of the caspase-3, -9 enzymes were increased in the treated cells. In vivo studies revealed that compounds 11g + 12g and 11h + 12h showed significant antitumor activity compared with controlled group. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.051

文献信息

• Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents
  作者：Wenfeng Wang、Zedong Bai、Fengsen Zhang、Conghui Wang、Yaofeng Yuan、Jingwei Shao

  DOI：10.1016/j.ejmech.2012.07.051

  日期：2012.10

  Twenty-six emodin derivatives (17 novel) which attach quaternary ammonium salt were synthesized and evaluated for their anticancer activities in vitro and in vivo. Compounds 11g + 12g and 11h + 12h had more significant antiproliferative ability against three cancer cell lines and low cytotoxicity to HELF. 11g + 12g and 11 h + 12h induced AGS cell apoptosis and arrested cell cycle at the G(0)/G(1) phase in a dose-dependent manner. Furthermore, the activities of the caspase-3, -9 enzymes were increased in the treated cells. In vivo studies revealed that compounds 11g + 12g and 11h + 12h showed significant antitumor activity compared with controlled group. (C) 2012 Elsevier Masson SAS. All rights reserved.