2-((2,3-ethylenedioxy-6,7-dimethoxyphenanthren-9-yl)methyl)-1H-pyrrole | 1375207-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2,3-ethylenedioxy-6,7-dimethoxyphenanthren-9-yl)methyl)-1H-pyrrole
• CAS: 1375207-51-4
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: RLBVOJBRJZRERN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((2,3-ethylenedioxy-6,7-dimethoxyphenanthren-9-yl)methyl)-1H-pyrrole 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 硫酸 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 12.0h， 以99.1%的产率得到2-((2,3-ethylenedioxy-6,7-dimethoxyphenanthren-9-yl)methyl)pyrrolidine
  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：

  2,3-ethylenedioxy-6,7-dimethoxyphenanthrene-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-ethylenedioxy-6,7-dimethoxyphenanthren-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