4,6-dimethyl-2-tetradecyl-1-(2-dodecanoylaminoethyl)pyridinium chloride

• 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: 4,6-dimethyl-2-tetradecyl-1-(2-dodecanoylaminoethyl)pyridinium chloride
• 英文别名: N-[2-(2,4-dimethyl-6-tetradecylpyridin-1-ium-1-yl)ethyl]dodecanamide;chloride
• 化学式: C₃₅H₆₅N₂O*Cl
• 分子量: 565.367
• InChiKey: PCYJPBZQGIYEIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  39
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  33
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,6-dimethyl-2-tetradecylpyrylium hexafluorophosphate 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.08h， 生成 4,6-dimethyl-2-tetradecyl-1-(2-dodecanoylaminoethyl)pyridinium chloride
  参考文献：
  名称：

  Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery

  摘要：

  Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.

  DOI：

  10.1021/jm0601755

文献信息

• Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery
  作者：Marc Antoniu Ilies、William A. Seitz、Betty H. Johnson、Edward L. Ezell、Aaron L. Miller、E. Brad Thompson、Alexandru T. Balaban

  DOI：10.1021/jm0601755

  日期：2006.6.1

  Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.