2,3-dimethoxy-6,7-ethylenedioxy-phenanthrene-9-carboxylic acid | 1234172-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dimethoxy-6,7-ethylenedioxy-phenanthrene-9-carboxylic acid
• 英文别名: 2,3-Dimethoxy-9,10-dihydronaphtho[2,1-g][1,4]benzodioxine-6-carboxylic acid
• CAS: 1234172-52-1
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: MBVDQZHGQHWRHR-UHFFFAOYSA-N

物化性质

• 熔点：
  280-283 °C
• 沸点：
  553.7±50.0 °C(predicted)
• 密度：
  1.377±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-6,7-ethylenedioxy-phenanthrene-9-carboxylic acid 在 sodium tetrahydroborate 、 草酰氯 、 N,N-二甲基甲酰胺 、 异丙醇 作用下， 反应 19.5h， 生成 2-((2,3-dimethoxy-6,7-ethylenedioxy-phenanthren-9-yl)methyl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents

  摘要：

  A series of phenanthroindolizidine and phenanthroquinolizidine alkaloids and their 14-amino-derivatives (1-44) were prepared and systematically evaluated for their anti-tumor activities against A549 and HL60 cell lines. The bioassay results showed that most of these alkaloids possess good anti-tumor activities. Especially, compounds 15, 22, 28, 33-36, 40 and 42 displayed low nanomolar or subnanomolar levels of anti-tumor activity. The configuration of (13aS,14S)-14-hydroxyphenanthroindolizidines and (14aR,15R)-15-hydroxyphenanthroquinolizidines was confirmed to be optimal. 14-Amino-phenanthroindolizidines with increased polarity possess good anti-tumor activity, especially for compounds 26 and 28. Most of the phenanthroquinolizidine alkaloids exhibited higher anti-tumor activity than that of phenanthroindolizidine alkaloids. Our present study provides fundamental support for development and optimization of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potential anti-tumor drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.048
• 作为产物：
  描述：

  (E)-2-(3,4-(ethylenedioxy)phenyl)-3-(3,4-dimethoxyphenyl)acrylic acid 在 manganese(IV) oxide 、 三氟乙酸 作用下， 反应 8.0h， 以88.1%的产率得到2,3-dimethoxy-6,7-ethylenedioxy-phenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents

  摘要：

  A series of phenanthroindolizidine and phenanthroquinolizidine alkaloids and their 14-amino-derivatives (1-44) were prepared and systematically evaluated for their anti-tumor activities against A549 and HL60 cell lines. The bioassay results showed that most of these alkaloids possess good anti-tumor activities. Especially, compounds 15, 22, 28, 33-36, 40 and 42 displayed low nanomolar or subnanomolar levels of anti-tumor activity. The configuration of (13aS,14S)-14-hydroxyphenanthroindolizidines and (14aR,15R)-15-hydroxyphenanthroquinolizidines was confirmed to be optimal. 14-Amino-phenanthroindolizidines with increased polarity possess good anti-tumor activity, especially for compounds 26 and 28. Most of the phenanthroquinolizidine alkaloids exhibited higher anti-tumor activity than that of phenanthroindolizidine alkaloids. Our present study provides fundamental support for development and optimization of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potential anti-tumor drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.048