4,7-喹啉二胺 | 40107-15-1

• 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
• 中文名称: 4,7-喹啉二胺
• 英文名称: 4,7-diaminoquinoline
• 英文别名: 4,7-Diaminochinolin；quinoline-4,7-diamine
• CAS: 40107-15-1
• 化学式: C₉H₉N₃
• 分子量: 159.191
• InChiKey: TWLGPWZTMALXOR-UHFFFAOYSA-N

物化性质

• 沸点：
  425.3±30.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4,7-喹啉二胺 在 溶剂黄146 作用下， 生成 N-(4-amino-[7]quinolyl)-acetamide
  参考文献：
  名称：

  Austin et al., Journal of Pharmacy and Pharmacology, 1959, vol. 11, p. 80,86

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙基(3-硝基苯胺亚甲基)丙二酸 在 盐酸 、 ammonium hydroxide 、 tin(ll) chloride 、 sodium hydroxide 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 二苯醚 、 水 、 溶剂黄146 为溶剂， 反应 21.0h， 生成 4,7-喹啉二胺
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040

文献信息

• METAL TRIANGULO COMPOUND AND METHODS OF USING THE SAME
  申请人：National University of Singapore

  公开号：EP2147005A1

  公开（公告）日：2010-01-27
• US8399447B2
  申请人：——

  公开号：US8399447B2

  公开（公告）日：2013-03-19
• [EN] METAL TRIANGULO COMPOUND AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉ TRIANGULO DE MÉTAL ET PROCÉDÉ D'UTILISATION DE CELUI-CI
  申请人：UNIV SINGAPORE

  公开号：WO2008127197A1

  公开（公告）日：2008-10-23

  [EN] The present invention relates to a metal triangulo compound. Provided is also a method of inducing apoptosis in a cell that comprises administering the metal triangulo compound. Provided is also a method of preventing carcinogenesis in a cell that comprises administering the metal triangulo compound.
  [FR] La présente invention concerne un composé triangulo de métal. L'invention concerne également un procédé d'induction de l'apoptose dans une cellule qui comprend l'administration du composé triangulo de métal. L'invention concerne également un procédé de prévention de la carcinogenèse dans une cellule, comprenant l'administration du composé triangulo de métal.
• Austin et al., Journal of Pharmacy and Pharmacology, 1959, vol. 11, p. 80,86
  作者：Austin et al.

  DOI：——

  日期：——
• Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods
  作者：Samkele Nsumiwa、David Kuter、Sergio Wittlin、Kelly Chibale、Timothy J. Egan

  DOI：10.1016/j.bmc.2013.04.040

  日期：2013.7

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.