4,4'-[1,6-(3,4-dithiahexane)]bispyridine | 2127-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-[1,6-(3,4-dithiahexane)]bispyridine
• 英文别名: 1,2-bis[2-(pyridin-4-yl)ethyl]disulfane；Bis-<2-(4-Pydridyl)-ethyl>-disulfid；2-(4-Pydridyl)-ethyl-disulfid；2-(4-Pyridyl)-ethyl-disulfid；4,4'-(3,4-dithia-hexane-1,6-diyl)-bis-pyridine；Bis(2-(4-pyridinyl)ethyl) disulfide；4-[2-(2-pyridin-4-ylethyldisulfanyl)ethyl]pyridine
• CAS: 2127-07-3
• 化学式: C₁₄H₁₆N₂S₂
• 分子量: 276.426
• InChiKey: LFNOKCRXVALZIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-[1,6-(3,4-dithiahexane)]bispyridine 、 硬脂基溴 以 乙醇 为溶剂， 反应 14.0h， 以8.5%的产率得到
  参考文献：
  名称：

  Biological and physicochemical properties of gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ

  摘要：

  We synthesized two novel gemini quaternary ammonium compounds (gemini QACs), 4,4'-[1,6-(2,5-dithiahexane)]bis(1-alkylpyridinium bromide) and 4,4'-[1,6-(3,4-dithiahexane)]bis(l-alkylpyridinium bromide), which are essentially two dimerized pyridinium salts. Three gemini QACs in which the positions of a cross-linking sulfur in the spacer differ, in addition to the previously described 4,4'-[1,6-(1,6-dithiahexane)]bis(1-alkylpyridinium bromide) to both gemini compounds, were determined for their antimicrobial, hemolytic and surface activities and molecular hydrophobicity. Comparative biological and physicochemical studies concluded that the position of sulfur in the spacer chain for three gemini QAC series influences the surface activity, the hydrophobicity and the electron density of the ammonium nitrogen, and that their biological properties are ascribable to the variation of these parameters caused by the position of the sulfur. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.015
• 作为产物：
  描述：

  4-吡啶乙硫醇盐酸盐 在 双氧水 、 potassium iodide 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 4,4'-[1,6-(3,4-dithiahexane)]bispyridine
  参考文献：
  名称：

  基于pH值的Ru基前药活化机理的研究

  摘要：

  基于Ru III的前药AziRu有效结合蛋白质，但其释放机理仍存在争议。在此，为了检验从蛋白质中还原介导的Ru释放的假说，在两个不同的氧化状态Ru II和Ru III中，拉曼辅助晶体学研究了AziRu与模型蛋白（蛋清溶菌酶）的结合，进行了。我们的结果表明Ru还原，但是还原后Ru的释放取决于还原剂。为了更好地理解该过程，还对AziRu-官能化的Au电极进行了pH依赖的光谱电化学表面增强拉曼散射（SERS）研究，作为Ru II-和Ru III的替代和最简单的模型系统。药物。这项SERS研究为Ru III态的水合AziRu提供了6.0±0.4的ap K a，该水落在pH值的分水岭范围内，使大多数癌症环境与生理环境分离开来。这些实验还表明，在酸化后，氧化还原电位E 0的变化幅度大于600 mV的含水AziRu朝着更正的电位方向移动，表明癌症管腔中选择性的AziRu降低，但在健康管腔中则没有。预期配

  DOI：

  10.1021/acs.inorgchem.8b02667

文献信息

• Kinetics and mechanism of the oxidation of n-dodecanethiol and pyridine-substituted ethanethiols by iodine molecule in acetonitrile
  作者：David L. De Leeuw、W. Kenneth Musker、Joyce Takahashi Doi

  DOI：10.1021/jo00146a008

  日期：1982.12
• On the pH-Modulated Ru-Based Prodrug Activation Mechanism
  作者：Marco Caterino、Mona Herrmann、Antonello Merlino、Claudia Riccardi、Daniela Montesarchio、Maria A. Mroginski、Domenica Musumeci、Francesco Ruffo、Luigi Paduano、Peter Hildebrandt、Jacek Kozuch、Alessandro Vergara

  DOI：10.1021/acs.inorgchem.8b02667

  日期：2019.1.22

  efficiently binds to proteins, but the mechanism of its release is still disputed. Herein, in order to test the hypothesis of a reduction-mediated Ru release from proteins, a Raman-assisted crystallographic study on AziRu binding to a model protein (hen egg white lysozyme), in two different oxidation states, RuII and RuIII, was carried out. Our results indicate Ru reduction, but the Ru release upon reduction

  基于Ru III的前药AziRu有效结合蛋白质，但其释放机理仍存在争议。在此，为了检验从蛋白质中还原介导的Ru释放的假说，在两个不同的氧化状态Ru II和Ru III中，拉曼辅助晶体学研究了AziRu与模型蛋白（蛋清溶菌酶）的结合，进行了。我们的结果表明Ru还原，但是还原后Ru的释放取决于还原剂。为了更好地理解该过程，还对AziRu-官能化的Au电极进行了pH依赖的光谱电化学表面增强拉曼散射（SERS）研究，作为Ru II-和Ru III的替代和最简单的模型系统。药物。这项SERS研究为Ru III态的水合AziRu提供了6.0±0.4的ap K a，该水落在pH值的分水岭范围内，使大多数癌症环境与生理环境分离开来。这些实验还表明，在酸化后，氧化还原电位E 0的变化幅度大于600 mV的含水AziRu朝着更正的电位方向移动，表明癌症管腔中选择性的AziRu降低，但在健康管腔中则没有。预期配
• Biological and physicochemical properties of gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ
  作者：Akihiro Shirai、Takuya Maeda、Hideaki Nagamune、Hitoshi Matsuki、Shoji Kaneshina、Hiroki Kourai

  DOI：10.1016/j.ejmech.2004.09.015

  日期：2005.1

  We synthesized two novel gemini quaternary ammonium compounds (gemini QACs), 4,4'-[1,6-(2,5-dithiahexane)]bis(1-alkylpyridinium bromide) and 4,4'-[1,6-(3,4-dithiahexane)]bis(l-alkylpyridinium bromide), which are essentially two dimerized pyridinium salts. Three gemini QACs in which the positions of a cross-linking sulfur in the spacer differ, in addition to the previously described 4,4'-[1,6-(1,6-dithiahexane)]bis(1-alkylpyridinium bromide) to both gemini compounds, were determined for their antimicrobial, hemolytic and surface activities and molecular hydrophobicity. Comparative biological and physicochemical studies concluded that the position of sulfur in the spacer chain for three gemini QAC series influences the surface activity, the hydrophobicity and the electron density of the ammonium nitrogen, and that their biological properties are ascribable to the variation of these parameters caused by the position of the sulfur. (C) 2004 Elsevier SAS. All rights reserved.