N-(2-{N-(2-aminoethyl)-N-[2-(N-{2,6-di-[N-(tert-butoxycarbonyl)amino]-1-oxohexyl}amino)ethyl]amino}ethyl)-2-hexadecyl-N'-[(9Z)-octadec-9-enyl]propane diamide | 1309877-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-{N-(2-aminoethyl)-N-[2-(N-{2,6-di-[N-(tert-butoxycarbonyl)amino]-1-oxohexyl}amino)ethyl]amino}ethyl)-2-hexadecyl-N'-[(9Z)-octadec-9-enyl]propane diamide
• CAS: 1309877-38-0
• 化学式: C₅₉H₁₁₅N₇O₇
• 分子量: 1034.6
• InChiKey: OMEZPQPDIYEQNO-FJVRRGAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.71
• 重原子数：
  73.0
• 可旋转键数：
  48.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  193.22
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(2-{N-(2-aminoethyl)-N-[2-(N-{2,6-di-[N-(tert-butoxycarbonyl)amino]-1-oxohexyl}amino)ethyl]amino}ethyl)-2-hexadecyl-N'-[(9Z)-octadec-9-enyl]propane diamide 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-[2-(N,N-bis{2-[N-(2,6-diamino-1-oxohexyl)amino]ethyl}amino)ethyl]-2-hexadecyl-N'-[(9Z)-octadec-9-enyl]propane diamide
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022
• 作为产物：
  描述：

  2-{[(9Z)-octadec-9-enylamino]carbonyl}octadecanoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(2-{N-(2-aminoethyl)-N-[2-(N-{2,6-di-[N-(tert-butoxycarbonyl)amino]-1-oxohexyl}amino)ethyl]amino}ethyl)-2-hexadecyl-N'-[(9Z)-octadec-9-enyl]propane diamide
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022