6-amino-2,4-dimethoxyphenanthridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-amino-2,4-dimethoxyphenanthridine
• 英文别名: 2,4-Dimethoxyphenanthridin-6-amine；2,4-dimethoxyphenanthridin-6-amine
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: PXVHCABTCHZABI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氯苯腈 、 2,4-二甲氧基苯胺 在 氨 、 sodium amide 、 lithium amide 作用下， 以 乙醚 为溶剂， 反应 4.5h， 以62%的产率得到6-amino-2,4-dimethoxyphenanthridine
  参考文献：
  名称：

  A single step synthesis of 6-aminophenanthridines from anilines and 2-chlorobenzonitriles

  摘要：

  Biologically active 6-aminophenanthridines were prepared in a single step procedure: Metal amides in liquid ammonia promoted the condensation of anilines with 2-chloro-benzonitriles. 6-Aminophenanthridines were isolated in moderate yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.062

文献信息

• Evaluation of the antiprion activity of 6-aminophenanthridines and related heterocycles
  作者：Phuhai Nguyen、Nassima Oumata、Flavie Soubigou、Justine Evrard、Nathalie Desban、Pascale Lemoine、Serge Bouaziz、Marc Blondel、Cécile Voisset

  DOI：10.1016/j.ejmech.2014.05.083

  日期：2014.7

  Series of 6-aminophenanthridines and related heterocyclic compounds such as benzonaphtyridines were prepared. Reduction of one of the three aromatic rings was also performed. The compounds were first tested for their antiprion activity in a previously described yeast-based colourimetric prion assay. The most potent derivatives were then assayed ex vivo against the mammalian prion PrPSc in a cell-based

  制备了一系列6-氨基菲啶和相关的杂环化合物，例如苯并萘啶。还进行了三个芳环之一的还原。首先在先前描述的基于酵母的比色病毒测定中测试化合物的抗pr病毒活性。然后在基于细胞的测定中针对哺乳动物病毒PrP Sc离体测定最有效的衍生物。发现几种新化合物比母体铅6-氨基菲啶更有效。对抗酵母和哺乳动物pr病毒最有前景的化合物是8-叠氮基-6-氨基菲啶（3m）和7,10-二氢菲啶-6-胺（14）。在基于哺乳动物细胞的测定中，IC 50 这两种化合物的分别分别约为5μM和1.8μM。
• A single step synthesis of 6-aminophenanthridines from anilines and 2-chlorobenzonitriles
  作者：Fabienne Gug、Stéphane Bach、Marc Blondel、Jean-Michel Vierfond、Anne-Sophie Martin、Hervé Galons

  DOI：10.1016/j.tet.2004.03.062

  日期：2004.5

  Biologically active 6-aminophenanthridines were prepared in a single step procedure: Metal amides in liquid ammonia promoted the condensation of anilines with 2-chloro-benzonitriles. 6-Aminophenanthridines were isolated in moderate yield. (C) 2004 Elsevier Ltd. All rights reserved.