2,3-dimethoxy-6,7-methylenedioxy-phenanthrene-9-carboxylic acid

• 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: 2,3-dimethoxy-6,7-methylenedioxy-phenanthrene-9-carboxylic acid
• 英文别名: 2,3-dimethoxy-phenanthro[2,3-d][1,3]dioxole-6-carboxylic acid；2,3-Dimethoxy-phenanthro[2,3-d][1,3]dioxol-6-carbonsaeure；2,3-Dimethoxynaphtho[2,1-f][1,3]benzodioxole-6-carboxylic acid
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: KUXPVEHZGWFIIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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-methylenedioxy-phenanthrene-9-carboxylic acid 在 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， 20.0 ℃ 、10.13 MPa 条件下， 反应 31.5h， 生成 2-((2,3-dimethoxy-6,7-methylenedioxy-phenanthren-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：

  methyl (2E)-2-(1,3-benzodioxol-5-yl)-3-(3,4-dimethoxyphenyl)acrylate 在 vanadium oxytrifluoride 、 三氟乙酸 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2,3-dimethoxy-6,7-methylenedioxy-phenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 1-phenanthryl-tetrahydroisoquinoline derivatives as novel p21-activated kinase 4 (PAK4) inhibitors

  摘要：

  通过对内部天然产物数据库的筛选，合成了作为新型PAK4抑制剂的1-苯并基四氢异喹啉类似物。

  DOI：

  10.1039/c5ob00037h

文献信息

• Shirai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, # 10, p. 517,527
  作者：Shirai

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of 1-phenanthryl-tetrahydroisoquinoline derivatives as novel p21-activated kinase 4 (PAK4) inhibitors
  作者：Shuai Song、Xiaodong Li、Jing Guo、Chenzhou Hao、Yan Feng、Bingyu Guo、Tongchao Liu、Qiaoling Zhang、Zhen Zhang、Ruijuan Li、Jian Wang、Bin Lin、Feng Li、Dongmei Zhao、Maosheng Cheng

  DOI：10.1039/c5ob00037h

  日期：——

  Following the screening of an in-house natural product database, 1-phenanthryltetrahydroisoquinoline analogues were synthesized as novel PAK4 inhibitors.

  通过对内部天然产物数据库的筛选，合成了作为新型PAK4抑制剂的1-苯并基四氢异喹啉类似物。
• 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.