N¹,N²-bis(7-chloroquinolin-4-yl)butane-1,4-diamine | 140926-78-9

• 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,N²-bis(7-chloroquinolin-4-yl)butane-1,4-diamine
• 英文别名: N,N'-bis-(7-chloro-[4]quinolyl)-butanediyldiamine；N,N'-Bis-(7-chlor-[4]chinolyl)-butandiyldiamin；N,N'-bis(7-chloroquinolin-4-yl)butane-1,4-diamine
• CAS: 140926-78-9
• 化学式: C₂₂H₂₀Cl₂N₄
• 分子量: 411.334
• InChiKey: VBZMFZHHLOVTDC-UHFFFAOYSA-N

物化性质

• 熔点：
  360 °C
• 沸点：
  649.4±55.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹,N²-bis(7-chloroquinolin-4-yl)butane-1,4-diamine 在 硝酸 作用下， 以86%的产率得到N,N'-Bis-(7-chloro-6-nitro-quinolin-4-yl)-butane-1,4-diamine
  参考文献：
  名称：

  Synthesis of bisquinolines and their in vitro ability to produce methemoglobin in canine hemolysate

  摘要：

  Synthesis of a number of derivatives of bisquinolines (3-9) have been reported here. Effect of these compounds on in vitro methemoglobin formation and methemoglobin reductase activity has resulted in the identification of two potential compounds (5 & 7), showing negligible methemoglobin toxicity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00058-x
• 作为产物：
  描述：

  4,7-二氯喹啉 、 四亚甲基二胺 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 N¹,N²-bis(7-chloroquinolin-4-yl)butane-1,4-diamine
  参考文献：
  名称：

  7-氯-4-（取代的氨基）喹啉的合成和抗丝概况：一类新的抗丝剂。

  摘要：

  描述了7-氯-4-（取代的氨基）喹啉（2-22）的合成及其抗丝活性。某些筛选出的化合物对啮齿动物雌性棘皮动物棘皮动物的丝虫反应和杀菌作用显示出良好的前景。

  DOI：

  10.1016/s0960-894x(00)00255-9

文献信息

• Bisquinolines. 1. N,N-bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine-resistant malaria
  作者：Jonathan L. Vennerstrom、William Y. Ellis、Arba L. Ager、Steven L. Andersen、Lucia Gerena、Wilbur K. Milhous

  DOI：10.1021/jm00089a025

  日期：1992.5

  On the basis of observations that several bisquinolines such as piperaquine possess notable activity against chloroquine-resistant malaria, 13 N,N-bis-(7-chloroquinolin-4-yl)alkanediamines were synthesized and screened against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Twelve of the thirteen bisquinolines had a significantly lower resistance index than did chloroquine; the resistance index was apparently unrelated to either in vitro or in vivo activity. Except for two compounds, there was a reasonable correlation between in vitro and in vivo activities. Seven of the thirteen bisquinolines had IC50's of less than 6 nM against both chloroquine-sensitive (D-6) and -resistant (W-2) clones of P. falciparum and were curative against P. berghei at doses of 640 mg/kg. In contrast to chloroquine, these bisquinolines did not show any toxic deaths at curative dose levels. Four bisquinolines, however, caused skin lesions at the site of injection. Maximum activity was seen in bisquinolines with a connecting bridge of two carbon atoms where decreased conformational mobility seemed to increase activity. Bisquinoline 3 ((+/-)-trans-N1,N2-bis(7-chloroquinolin-4-yl)cyclohexane-1,2-diamine was not only the most potent bisquinoline in vitro, but was clearly unique in its in vivo activity-80% and 100% cure rates were achieved at doses of 160 and 320 mg/kg, respectively. In summary, these preliminary results support the premise that bisquinolines may be useful agents against chloroquine-resistant malaria.
• US2816893
  申请人：——

  公开号：——

  公开（公告）日：——