N¹-(2-aminoethyl)-N²-(7-chloro-4-quinolyl)-N¹-{2-[(7-chloro-4-quinolyl)amino]ethyl}-1,2-ethanediamine | 20903-71-3

• 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: N¹-(2-aminoethyl)-N²-(7-chloro-4-quinolyl)-N¹-{2-[(7-chloro-4-quinolyl)amino]ethyl}-1,2-ethanediamine
• 英文别名: 7-chloro-4-[10-(7-chloroquinolin-4-yl)-1,4,7,10-tetraazadecan-1-yl]quinoline；4,4'-(3,6-Diaza-octamethylendiamino)-bis-(7-chlor-chinolin)；N,N'-bis[2-[(7-chloroquinolin-4-yl)amino]ethyl]ethane-1,2-diamine
• CAS: 20903-71-3
• 化学式: C₂₄H₂₆Cl₂N₆
• 分子量: 469.417
• InChiKey: WLZLGTBHWPHETH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.9
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 、 三乙烯四胺 以28%的产率得到N¹-(2-aminoethyl)-N²-(7-chloro-4-quinolyl)-N¹-{2-[(7-chloro-4-quinolyl)amino]ethyl}-1,2-ethanediamine
  参考文献：
  名称：

  一系列双喹啉和双吡咯并[1,2a]喹喔啉化合物的合成及体外抗疟活性

  摘要：

  合成了含有各种多胺连接基的一系列双喹啉4-15和双吡咯并[1,2a]喹喔啉16-20。通过实验确定了水溶性和分布系数。筛选了化合物和氯喹对恶性疟原虫的D10和Dd2菌株的抗疟活性。对多种癌细胞系评估了双化合物4–9的生长抑制作用。发现水溶性随着潜在的质子化位点的增加而增加。双喹啉8和9分别具有三亚乙基四胺和N，N'-双（3-氨基丙基）乙二胺连接基的化合物是所有合成化合物中活性最高的。发现它们对氯丹抗D10一样有效，但对Dd2菌株则更有效，对寄生细胞具有良好的选择性。含有二亚乙基三胺桥的化合物4显示了该系列中最重要的抗癌活性，并且比依托泊苷对所有三种TK10，UACC62和MCF7癌细胞系均具有更有效的抗增殖抑制剂。

  DOI：

  10.1016/j.ejmech.2012.07.037

文献信息

• Antiplasmodial Activity and Cytotoxicity of Bis-, Tris-, and Tetraquinolines with Linear or Cyclic Amino Linkers
  作者：Sophie Girault、Philippe Grellier、Amaya Berecibar、Louis Maes、Pascal Lemière、Elisabeth Mouray、Elisabeth Davioud-Charvet、Christian Sergheraert

  DOI：10.1021/jm001096a

  日期：2001.5.1

  Bisquinoline heteroalkanediamines were structurally modified in order to study the effects of enhanced bulkiness and rigidity on both their activity on strains of Plasmodium falciparum expressing different degrees of chloroquine (CQ) resistance and their cytotoxicity toward mammalian cells. While cyclization yielded molecules of greater rigidity that were not more active than their linear counterparts, they were characterized by an absence of cytotoxicity. Alternatively, dimerization of these compounds led to tetraquinolines that are very potent for CQ-resistant strains and noncytotoxic.
• NOVEL BISAMINOQUINOLINE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS PREPARED THEREFROM AND THEIR USE
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US20170166530A1

  公开（公告）日：2017-06-15

  The present invention relates to novel bisaminoquinoline compounds, pharmaceutical compositions comprising these novel compounds and methods for inhibiting autophagy in biological systems. Methods of treating cancer in patients in need using compounds and/or compositions according to the present invention alone or in combination with at least one additional anticancer agent represent additional aspects of the invention. Methods of treating disease states and/or conditions in which inhibition of autophagy plays a favorable treatment role including rheumatoid arthritis, malaria, antiphospholipid antibody syndrome, lupus, chronic urticaria and Sjogren's disease, with compounds according to the present invention represent additional aspects of the invention.