4-hydroxy-2-(2-naphthyl)quinoline p-toluenesulfonate

• 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: 4-hydroxy-2-(2-naphthyl)quinoline p-toluenesulfonate
• 英文别名: 2-(2-naphthyl)-4-[(p-tolylsulfonyl)oxy]quinoline；(2-Naphthalen-2-ylquinolin-4-yl) 4-methylbenzenesulfonate
• 化学式: C₂₆H₁₉NO₃S
• 分子量: 425.508
• InChiKey: PIASYDHPAJSCNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲氨基氯乙烷盐酸 、 4-hydroxy-2-(2-naphthyl)quinoline p-toluenesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到4-[2-(dimethylamino)ethoxy]-2-(2-naphthyl)quinoline
  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：

  2-(2-萘基)-4-羟基喹啉对甲苯磺酸盐 在 碳酸氢钠 作用下， 以 吡啶 、 盐酸 、 水 为溶剂， 以3.5 g (79%)的产率得到4-hydroxy-2-(2-naphthyl)quinoline p-toluenesulfonate
  参考文献：
  名称：

  Antagonism of immunostimulatory CpG-oligonucleotides by 4-aminoquinolines and other weak bases

  摘要：

  本发明一般涉及免疫学领域。更具体地涉及抑制免疫系统刺激的组合物和方法。这些化合物和方法包括类似氯喹的衍生物和类似物，如4-氨基喹啉和其他弱碱性物质。它们可用于自身免疫性疾病和现象、移植排斥如宿主对移植物疾病以及败血症的预防和治疗。

  公开号：

  US06479504B1

文献信息

• ANTAGONISM OF IMMUNOSTIMULATORY CPG-OLIGONUCLEOTIDES BY 4-AMINOQUINOLINES AND OTHER WEAK BASES
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：EP1377554A1

  公开（公告）日：2004-01-07
• US6479504B1
  申请人：——

  公开号：US6479504B1

  公开（公告）日：2002-11-12
• [EN] ANTAGONISM OF IMMUNOSTIMULATORY CPG-OLIGONUCLEOTIDES BY 4-AMINOQUINOLINES AND OTHER WEAK BASES<br/>[FR] ANTAGONISME DES OLIGONUCLEOTIDES CPG IMMUNOSTIMULATEURS PAR DES 4-AMINOQUINOLINES ET AUTRES BASES FAIBLES
  申请人：UNIV IOWA STATE RES FOUND

  公开号：WO2000076982A1

  公开（公告）日：2000-12-21

  The present invention relates generally to the field of immunology. More particularly it concerns compositions and methods for inhibiting stimulation of the immune system. The compounds and methods comprise compounds that are analogs and derivatives of chloroquine, such as 4-aminoquinolines, and other weak bases. They can be used in preventative and therapeutic treatments of autoimmune diseases and phenomena, transplant rejection such as host-versus-graft disease, and sepsis.
• Triplex Selective 2-(2-Naphthyl)quinoline Compounds:  Origins of Affinity and New Design Principles
  作者：Jonathan B. Chaires、Jinsong Ren、Maged Henary、Oliwia Zegrocka、G. Reid Bishop、Lucjan Strekowski

  DOI：10.1021/ja034181r

  日期：2003.6.1

  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.
• Antagonism of immunostimulatory CpG-oligonucleotides by 4-aminoquinolines and other weak bases
  申请人：The University of Iowa Research Foundation

  公开号：US06479504B1

  公开（公告）日：2002-11-12

  The present invention relates generally to the field of immunology. More particularly it concerns compositions and methods for inhibiting stimulation of the immune system. The compounds and methods comprise compounds that are analogs and derivatives of chloroquine, such as 4-aminoquinolines, and other weak bases. They can be used in preventative and therapeutic treatments of autoimmune diseases and phenomena, transplant rejection such as host-versus-graft disease, and sepsis.

  本发明一般涉及免疫学领域。更具体地涉及抑制免疫系统刺激的组合物和方法。这些化合物和方法包括类似氯喹的衍生物和类似物，如4-氨基喹啉和其他弱碱性物质。它们可用于自身免疫性疾病和现象、移植排斥如宿主对移植物疾病以及败血症的预防和治疗。