14,17,24,27-Tetraoxa-4-azaheptacyclo[19.8.0.02,10.04,8.011,20.013,18.023,28]nonacosa-1(29),2(10),11,13(18),19,21,23(28)-heptaene | 1034897-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 14,17,24,27-Tetraoxa-4-azaheptacyclo[19.8.0.02,10.04,8.011,20.013,18.023,28]nonacosa-1(29),2(10),11,13(18),19,21,23(28)-heptaene
• CAS: 1034897-90-9
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: LCQXBJBYAFGUBG-UHFFFAOYSA-N

物化性质

• 熔点：
  263-266 °C (decomp)
• 沸点：
  598.7±39.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-ethylenedioxy-6,7-ethylenedioxy-phenanthrene-9-carboxylic acid 在 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、10.13 MPa 条件下， 反应 46.5h， 生成 14,17,24,27-Tetraoxa-4-azaheptacyclo[19.8.0.02,10.04,8.011,20.013,18.023,28]nonacosa-1(29),2(10),11,13(18),19,21,23(28)-heptaene
  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

文献信息

• Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents
  作者：Ziwen Wang、Meng Wu、Yi Wang、Zheng Li、Lei Wang、Guifang Han、Fazhong Chen、Yuxiu Liu、Kailiang Wang、Ao Zhang、Linghua Meng、Qingmin Wang

  DOI：10.1016/j.ejmech.2012.02.048

  日期：2012.5

  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.