2,3-methylenedioxy-6,7-dimethoxyphenanthrene-9-carboxylic acid | 1234172-48-5

• 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-methylenedioxy-6,7-dimethoxyphenanthrene-9-carboxylic acid
• 英文别名: 2,3-Dimethoxynaphtho[2,1-f][1,3]benzodioxole-5-carboxylic acid；2,3-dimethoxynaphtho[2,1-f][1,3]benzodioxole-5-carboxylic acid
• CAS: 1234172-48-5
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: LWTKHJBSMRCPIY-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-methylenedioxy-6,7-dimethoxyphenanthrene-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 13,14-Dimethoxy-20,22-dioxa-4-azahexacyclo[15.7.0.02,10.04,8.011,16.019,23]tetracosa-1(24),2(10),11,13,15,17,19(23)-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
• 作为产物：
  描述：

  (E)-2-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)acrylic acid 在 二叔丁基过氧化物 作用下， 以 乙腈 、 三氟乙酸 为溶剂， 反应 4.0h， 以86.4%的产率得到2,3-methylenedioxy-6,7-dimethoxyphenanthrene-9-carboxylic acid
  参考文献：
  名称：

  二叔丁基过氧化物促进的2,3-二取代苯基丙烯酸及其衍生物的氧化分子内偶联

  摘要：

  聚甲氧基取代的菲-9羧酸或其甲酯是合成tylophora生物碱及其类似物的关键中间体。未官能化的2，3-二取代的苯基丙烯酸和过氧化二叔丁基促进的衍生物的分子内氧化偶联反应以高收率得到上述中间体。该方法温和的反应条件和简便的纯化步骤为合成菲提供了一种新方法。

  DOI：

  10.1016/j.cclet.2013.11.004

文献信息

• 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。
• Iron(III) Chloride Catalyzed Oxidative Coupling Reaction of 1,2-Diarylethylene Derivatives
  作者：Derong Ji、Lidan Su、Keqing Zhao、Biqin Wang、Ping Hu、Chun Feng、Shikai Xiang、Hua Yang、Chenggang Zhang

  DOI：10.1002/cjoc.201300308

  日期：2013.8

  A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2‐diarylethylene derivatives with di‐tert‐butylperoxide (DTBP) as a sole oxidant at room temperature in CH2Cl2/TFA (9:1 V/V) to yield phenanthrenes in good to excellent yields

  开发了一种无毒的FeCl 3催化的分子内氧化偶联反应，用于轻度合成一系列具有不同取代基的菲。该方法涉及在室温下在CH 2 Cl 2 / TFA（9：1 V / V）中将多种1,2-二芳基乙烯衍生物与二叔丁基过氧化物（DTBP）作为唯一氧化剂进行交叉脱氢偶联以生成菲产量高到极好。
• Oxidative intramolecular coupling of 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide
  作者：De-Rong Ji、Hua Yang、Xiao-Jing Zhao、Hao Yang、Yang-Zhao Liu、Dai-Hui Liao、Chun Feng、Cheng-Gang Zhang

  DOI：10.1016/j.cclet.2013.11.004

  日期：2014.2

  Polymethoxy-substituted phenanthrene-9-carboxylic acids or their methylate are key intermediates for the synthesis of tylophora alkaloids and their analogs. An intramolecular oxidative coupling reaction of unfunctionalized 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide gave above intermediates in high yields. The mild reaction conditions and easy purification

  聚甲氧基取代的菲-9羧酸或其甲酯是合成tylophora生物碱及其类似物的关键中间体。未官能化的2，3-二取代的苯基丙烯酸和过氧化二叔丁基促进的衍生物的分子内氧化偶联反应以高收率得到上述中间体。该方法温和的反应条件和简便的纯化步骤为合成菲提供了一种新方法。
• 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.