N,N-bis(6-chloro-2-methoxy-9-acridinyl)-1,8-octanediamine | 67047-12-5

• 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: N,N-bis(6-chloro-2-methoxy-9-acridinyl)-1,8-octanediamine
• 英文别名: N,N'-bis(6-chloro-2-methoxyacridin-9-yl)octane-1,8-diamine
• CAS: 67047-12-5
• 化学式: C₃₆H₃₆Cl₂N₄O₂
• 分子量: 627.613
• InChiKey: PJKQWFZYJDFYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  68.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,8-辛二胺 、 6,9-二氯-2-甲氧基吖啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-bis(6-chloro-2-methoxy-9-acridinyl)-1,8-octanediamine
  参考文献：
  名称：

  Antimalarial, Antitrypanosomal, and Antileishmanial Activities and Cytotoxicity of Bis(9-amino-6-chloro-2-methoxyacridines):  Influence of the Linker

  摘要：

  Forty bis(9-amino-6-chloro-2-methoxyacridines), in which acridine moieties are joined by alkanediamines, polyamines, or polyamines substituted by a side chain, were synthesized and tested for their in vitro activity upon the erythrocytic stage of Plasmodium falciparum, trypomastigote stage of Trypanosoma brucei, and amastigote stage of Trypanosoma cruzi and Leishmania infantum as well as for their cytotoxic effects upon MRC-5 cells. Results clearly showed the importance of the nature of the linker and of its side chain for antiparasitic activity, cytotoxicity, and cellular localization. Among several compounds devoid of cytotoxic effects at 25 mu M upon MRC-5 cells, one displayed IC50 values ranging from 8 to 18 nM against different P. falciparum strains while three others totally inhibited T. brucei at 1.56 mu M.

  DOI：

  10.1021/jm990946n

文献信息

• Synthesis of Monomeric and Dimeric Acridine Compounds as Potential Therapeutics in Alzheimer and Prion Diseases
  作者：René Csuk、Alexander Barthel、Christian Raschke、Ralph Kluge、Dieter Ströhl、Lothar Trieschmann、Gerald Böhm

  DOI：10.1002/ardp.200900065

  日期：2009.12

  spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion‐ and Alzheimer‐specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis‐acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4‐dimethoxy‐6‐nitro compound 7h for

  从取代的 9-氯吖啶开始，制备了一系列奎纳克林和间隔二聚吖啶化合物。使用基于 FACS 分析的快速筛选系统探索了它们中断朊病毒和阿尔茨海默特异蛋白与 Ab 肽的蛋白质结合的能力。双吖啶比相应的单体表现出更高的活性。在这些衍生物中，Aβ-肽的 2,4-二甲氧基-6-硝基化合物 7h 和 PrP 的 2-甲氧基-6-硝基化合物 7f 获得了最好的结果。
• Antimalarial, Antitrypanosomal, and Antileishmanial Activities and Cytotoxicity of Bis(9-amino-6-chloro-2-methoxyacridines):  Influence of the Linker
  作者：Sophie Girault、Philippe Grellier、Amaya Berecibar、Louis Maes、Elisabeth Mouray、Pascal Lemière、Marie-Ange Debreu、Elisabeth Davioud-Charvet、Christian Sergheraert

  DOI：10.1021/jm990946n

  日期：2000.7.1

  Forty bis(9-amino-6-chloro-2-methoxyacridines), in which acridine moieties are joined by alkanediamines, polyamines, or polyamines substituted by a side chain, were synthesized and tested for their in vitro activity upon the erythrocytic stage of Plasmodium falciparum, trypomastigote stage of Trypanosoma brucei, and amastigote stage of Trypanosoma cruzi and Leishmania infantum as well as for their cytotoxic effects upon MRC-5 cells. Results clearly showed the importance of the nature of the linker and of its side chain for antiparasitic activity, cytotoxicity, and cellular localization. Among several compounds devoid of cytotoxic effects at 25 mu M upon MRC-5 cells, one displayed IC50 values ranging from 8 to 18 nM against different P. falciparum strains while three others totally inhibited T. brucei at 1.56 mu M.