N¹,N²-bis(7-chloroquinolin-4-yl)hexane-1,6-diamine | 140926-81-4

• 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)hexane-1,6-diamine
• 英文别名: N¹,N⁶-bis(7-chloroquinolin-4-yl)hexane-1,6-diamine；N,N'-bis-(7-chloro-[4]quinolyl)-hexanediyldiamine；N,N'-Bis-(7-chlor-[4]chinolyl)-hexandiyldiamin；N,N'-bis(7-chloro-4-quinolyl)hexane-1,6-diamine；N,N'-bis(7-chloroquinolin-4-yl)hexane-1,6-diamine
• CAS: 140926-81-4
• 化学式: C₂₄H₂₄Cl₂N₄
• 分子量: 439.387
• InChiKey: HHWIMTYEHYWKEK-UHFFFAOYSA-N

物化性质

• 熔点：
  280-281 °C
• 沸点：
  661.3±55.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-己二胺 、 4,7-二氯喹啉 在 苯酚 作用下， 生成 N¹,N²-bis(7-chloroquinolin-4-yl)hexane-1,6-diamine
  参考文献：
  名称：

  US2816893

  摘要：

  公开号：

文献信息

• US2816893
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] METHODS OF FACILITATING NEURAL CELL SURVIVAL USING GDNF FAMILY LIGAND (GFL) MIMETICS OR RET SIGNALING PATHWAY ACTIVATORS<br/>[FR] PROCÉDÉS DESTINÉS À FACILITER LA SURVIE DE CELLULES NEURONALES EN UTILISANT DES MIMÉTIQUES DE LIGANDS DE LA FAMILLE DES GDNF (GFL) OU DES ACTIVATEURS DE LA VOIE DE SIGNALISATION DU RET
  申请人：BALTIC TECHNOLOGY DEV LTD

  公开号：WO2011070177A2

  公开（公告）日：2011-06-16

  Disclosed are compounds and methods for treating neurological and other disorders by administering to a subject in need thereof an effective amount of a compound having binding and/or modulation specificity for GFRα receptor molecules, which can be mimetics of glial-derived neurotrophic factor (GDNF) family ligands (GFLs), GFRα/RET signaling pathway agonists, and/or direct RET agonists (activators).
• 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.