bis((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl) 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate) | 1370264-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bis((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl) 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate)
• CAS: 1370264-05-3
• 化学式: C₇₄H₁₂₄N₂O₁₀S₂
• 分子量: 1265.94
• InChiKey: RIXJHUJDYPOBNG-FWBFXEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.26
• 重原子数：
  88.0
• 可旋转键数：
  35.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  147.72
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  bis((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl) 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate) 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 水 、 甲醇 为溶剂， 反应 7.0h， 以86.9%的产率得到
  参考文献：
  名称：

  Synthesis and Gene Transfer Activities of Novel Serum Compatible Reducible Tocopherol-Based Cationic Lipids

  摘要：

  The molecular structure of the cationic lipids greatly influences their transfection efficiency. High transfection efficiencies of tocopherol-based simple monocationic transfection lipids with hydroxylethyl headgroups were recently reported by us (Kedika, B., et al. J. Med. Chem. 2011, 54 (2), 548-561). Toward enhancing the transfection efficiency of tocopherol-based lipids, we have synthesized two tocopherol-based dicationic lipids (1 and 2) using simple cystine in the headgroup region. The efficiency of tocopherol-based lipids (1 and 2) were compared with nontocopherol-based lipids (3 and 4) with cystine in the headgroup region. We report also a comprehensive structure-activity relationship study that identified tocopherol-based gemini cationic lipid 1 is a better transfecting agent than its monomeric lipid counterpart 2 and two other nontocopherol-based gemini cationic lipids (3 and 4). The transfection efficiency of lipid 1 was also greater than that of commercial formulation in HepG2 cell lines. A major characteristic feature of this investigation is that serum does not inhibit the transfection activity of tocopherol-based lipids (1 and 2) in general and in particular lipid 1 which is found to be highly serum-compatible even at higher concentrations of serum when compared to its monomeric counterpart lipid 2 and the other two control lipid analogues 3 and 4.

  DOI：

  10.1021/mp200435y
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 40.5h， 生成 bis((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl) 3,3'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)propanoate)
  参考文献：
  名称：

  Cationic gemini lipids with cyclen headgroups: interaction with DNA and gene delivery abilities

  摘要：

  合成了十一种双子星阳离子脂质和一种单体对应物，并研究了它们作为非病毒基因载体的结构-活性关系。

  DOI：

  10.1039/c4ra05974c