N-(4-((4,5-dihydroxy-7-methyl-9,10-anthraquinone-2-yl)oxy)butyl)-N,N-dimethylhexadecan-1-aminium bromide | 1412421-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(4-((4,5-dihydroxy-7-methyl-9,10-anthraquinone-2-yl)oxy)butyl)-N,N-dimethylhexadecan-1-aminium bromide
• 英文别名: 4-(4,5-Dihydroxy-7-methyl-9,10-dioxoanthracen-2-yl)oxybutyl-hexadecyl-dimethylazanium;bromide；4-(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-2-yl)oxybutyl-hexadecyl-dimethylazanium;bromide
• CAS: 1412421-88-5
• 化学式: Br*C₃₇H₅₆NO₅
• 分子量: 674.759
• InChiKey: BDIYPCKDRPWQIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  大黄素 在 potassium carbonate 作用下， 以 乙二醇甲醚 、 丙酮 为溶剂， 反应 12.0h， 生成 N-(4-((4,5-dihydroxy-7-methyl-9,10-anthraquinone-2-yl)oxy)butyl)-N,N-dimethylhexadecan-1-aminium bromide
  参考文献：
  名称：

  Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives

  摘要：

  A series of new emodin derivatives modified at the C-3 and the C-6 positions were synthesized, and evaluated for their anticancer activities in vitro and in vivo. Among them, Compounds 5g and 5h had more significant antiproliferative ability against HepG2, BGC-823, AGS cancer cell lines and low cytotoxicity to HELF normal cell line, respectively. Compounds 5g and 5h induced AGS cell cycle arrest at G0/G1 phase and induce apoptosis via activation of caspase-3 and caspase-9 enzyme. In vivo studies using H22 xenografts in Kunming mice were conducted with 5g and 5h. The results revealed that the medium dosage group (10 mg/kg) of 5g and the high dosage group (25 mg/kg) of 5h showed significant antitumor activity compared to the control group. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.047

文献信息

• Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives
  作者：Jingwei Shao、Fengsen Zhang、Zedong Bai、Conghui Wang、Yaofeng Yuan、Wenfeng Wang

  DOI：10.1016/j.ejmech.2012.07.047

  日期：2012.10

  A series of new emodin derivatives modified at the C-3 and the C-6 positions were synthesized, and evaluated for their anticancer activities in vitro and in vivo. Among them, Compounds 5g and 5h had more significant antiproliferative ability against HepG2, BGC-823, AGS cancer cell lines and low cytotoxicity to HELF normal cell line, respectively. Compounds 5g and 5h induced AGS cell cycle arrest at G0/G1 phase and induce apoptosis via activation of caspase-3 and caspase-9 enzyme. In vivo studies using H22 xenografts in Kunming mice were conducted with 5g and 5h. The results revealed that the medium dosage group (10 mg/kg) of 5g and the high dosage group (25 mg/kg) of 5h showed significant antitumor activity compared to the control group. (C) 2012 Elsevier Masson SAS. All rights reserved.