6-[4-(2-Dimethylamino-ethylamino)-quinolin-2-yl]-naphthalen-2-ol | 313825-03-5

• 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: 6-[4-(2-Dimethylamino-ethylamino)-quinolin-2-yl]-naphthalen-2-ol
• CAS: 313825-03-5
• 化学式: C₂₃H₂₃N₃O
• 分子量: 357.455
• InChiKey: BMMJFEHNMUPNPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.39
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-[4-(2-Dimethylamino-ethylamino)-quinolin-2-yl]-naphthalen-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 N-[(2-dimethylamino)ethyl]-2-[6-[(6-hydroxyhexyl)oxy]-2-naphthyl]quinolin-4-amine
  参考文献：
  名称：

  Triplex Selective 2-(2-Naphthyl)quinoline Compounds:  Origins of Affinity and New Design Principles

  摘要：

  A novel competition dialysis assay was used to investigate the structural selectivity of a series of substituted 2-(2-naphthyl)quinoline compounds designed to target triplex DNA. The interaction of 14 compounds with 13 different nucleic acid sequences and structures was studied. A striking selectivity for the triplex structure poly dA:[poly dT](2) was found for the majority of compounds studied. Quantitative analysis of the competition dialysis binding data using newly developed metrics revealed that these compounds are among the most selective triplex-binding agents synthesized to date. A quantitative structure-affinity relationship (QSAR) was derived using triplex binding data for all 14 compounds used in these studies. The QSAR revealed that the primary favorable determinant of triplex binding free energy is the solvent accessible surface area. Triplex binding affinity is negatively correlated with compound electron affinity and the number of hydrogen bond donors. The QSAR provides guidelines for the design of improved triplex-binding agents.

  DOI：

  10.1021/ja034181r
• 作为产物：
  描述：

  N'-[2-(6-Methoxy-naphthalen-2-yl)-quinolin-4-yl]-N,N-dimethyl-ethane-1,2-diamine 在 三溴化硼 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 72.0h， 以89%的产率得到6-[4-(2-Dimethylamino-ethylamino)-quinolin-2-yl]-naphthalen-2-ol
  参考文献：
  名称：

  Triplex Selective 2-(2-Naphthyl)quinoline Compounds:  Origins of Affinity and New Design Principles

  摘要：

  A novel competition dialysis assay was used to investigate the structural selectivity of a series of substituted 2-(2-naphthyl)quinoline compounds designed to target triplex DNA. The interaction of 14 compounds with 13 different nucleic acid sequences and structures was studied. A striking selectivity for the triplex structure poly dA:[poly dT](2) was found for the majority of compounds studied. Quantitative analysis of the competition dialysis binding data using newly developed metrics revealed that these compounds are among the most selective triplex-binding agents synthesized to date. A quantitative structure-affinity relationship (QSAR) was derived using triplex binding data for all 14 compounds used in these studies. The QSAR revealed that the primary favorable determinant of triplex binding free energy is the solvent accessible surface area. Triplex binding affinity is negatively correlated with compound electron affinity and the number of hydrogen bond donors. The QSAR provides guidelines for the design of improved triplex-binding agents.

  DOI：

  10.1021/ja034181r