N,N′-bis(4-quinolinyl)pentane-1,5-diamine | 104772-00-1

• 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(4-quinolinyl)pentane-1,5-diamine
• 英文别名: 1,5-Pentanediamine, N,N-di-4-quinolinyl-；N,N'-di(quinolin-4-yl)pentane-1,5-diamine
• CAS: 104772-00-1
• 化学式: C₂₃H₂₄N₄
• 分子量: 356.47
• InChiKey: WTEQYWCGKHXBEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  610.3±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1,5-二碘戊烷 、 N,N′-bis(4-quinolinyl)pentane-1,5-diamine 以 丁酮 为溶剂， 反应 168.0h， 生成
  参考文献：
  名称：

  Bis-Quinolinium Cyclophanes:  8,14-Diaza-1,7(1,4)-diquinolinacyclotetradecaphane (UCL 1848), a Highly Potent and Selective, Nonpeptidic Blocker of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channel

  摘要：

  DOI：

  10.1021/jm000904v
• 作为产物：
  描述：

  4-氯喹啉 、 1,5-二氨基戊烷 以 戊醇 为溶剂， 反应 48.0h， 生成 N,N′-bis(4-quinolinyl)pentane-1,5-diamine
  参考文献：
  名称：

  Bis-quinolinium cyclophanes: toward a pharmacophore model for the blockade of apamin-sensitive SKCa channels in sympathetic neurons

  摘要：

  The synthesis, pharmacological evaluation, and molecular modeling studies of unsymmetrical bis-alkylene bis-quinolinium cyclophanes and xylylene-alkylene bis-quinolinium cyclophanes is described. Two important structural features of the pharmacophore for SKCa channel blockade have been identified. These are (i) an optimum distance of ca. 5.8 Angstrom between the centroids of the pyridinium rings of the two quinolinium groups and (ii) a preference for conformations having the quinolinium groups in a synperiplanar orientation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.011

文献信息

• Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
  作者：Donglai Yang、Lejla Arifhodzic、C. Robin Ganellin、Donald H. Jenkinson

  DOI：10.1016/j.ejmech.2013.02.029

  日期：2013.5

  Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking

  以前，已证明基于喹啉鎓的四氮杂环烷酮（例如UCL 1684和UCL 1848）作为有效的小肽非肽类阻滞剂，对化学结构的变化（尤其是对环庚烷体系的大小）非常敏感。电导Ca 2+激活的K +离子通道（SK Ca）。当前的工作试图优化UCL 1848中连接链的结构。我们报道了29个UCL 1848类似物的合成和SK Ca通道阻滞活性，其中UCL 1848的中心CH 2被其他基团X或取代。 Y = O，S，CF 2，C O，CHOH，C C，CHCH，CHMe，以探索键长或柔韧性的细微变化是否可以进一步提高效力。通过合成和测试带有取代基（NO 2，NH 2，CF 3，F，Cl，CH 3，OCH 3，OCF 3， OH）在氨基喹啉鎓环的5、6或7个位置上。与我们之前的工作一样，测定了每种化合物对大鼠交感神经元后超极化（AHP）的抑制作用，这种作用是由SK Ca通道的SK3亚型介导的。一种新化合物（39，R
• [EN] AUTOPHAGY-INHIBITING COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBANT L'AUTOPHAGIE ET LEURS UTILISATIONS
  申请人：PRESAGE BIOSCIENCES INC

  公开号：WO2016196393A2

  公开（公告）日：2016-12-08

  The present disclosure describes a compound for use in the treatment of cancer, infectious disease, and autoimmune disorders. The compounds herein can inhibit autophagy in an affected cell to promote cell death. Further, the compound can be used to overcome the drug-resistance of certain cells.
• Bis-quinolinium cyclophanes: toward a pharmacophore model for the blockade of apamin-sensitive SKCa channels in sympathetic neurons
  作者：Dimitrios Galanakis、C.Robin Ganellin、Jian-Quing Chen、Diyan Gunasekera、Philip M Dunn

  DOI：10.1016/j.bmcl.2004.06.011

  日期：2004.8

  The synthesis, pharmacological evaluation, and molecular modeling studies of unsymmetrical bis-alkylene bis-quinolinium cyclophanes and xylylene-alkylene bis-quinolinium cyclophanes is described. Two important structural features of the pharmacophore for SKCa channel blockade have been identified. These are (i) an optimum distance of ca. 5.8 Angstrom between the centroids of the pyridinium rings of the two quinolinium groups and (ii) a preference for conformations having the quinolinium groups in a synperiplanar orientation. (C) 2004 Elsevier Ltd. All rights reserved.
• Bis-Quinolinium Cyclophanes:  8,14-Diaza-1,7(1,4)-diquinolinacyclotetradecaphane (UCL 1848), a Highly Potent and Selective, Nonpeptidic Blocker of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channel
  作者：Jian-Qing Chen、Dimitrios Galanakis、C. Robin Ganellin、Philip M. Dunn、Donald H. Jenkinson

  DOI：10.1021/jm000904v

  日期：2000.9.1