N-(2-(dimethylamino)ethyl)-4,5-bis(dodecylthio)pentanamide | 1400773-20-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2-(dimethylamino)ethyl)-4,5-bis(dodecylthio)pentanamide
• 英文别名: N-[2-(dimethylamino)ethyl]-4,5-bis(dodecylsulfanyl)pentanamide
• CAS: 1400773-20-7
• 化学式: C₃₃H₆₈N₂OS₂
• 分子量: 573.048
• InChiKey: YVWPBXGPSUWRMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  38
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(dimethylamino)ethyl)-4,5-bis(dodecylthio)pentanamide 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 N-(2-(dimethylamino)ethyl)-4,5-bis(dodecylsulfonyl)pentanamide
  参考文献：
  名称：

  [EN] AMINO LIPIDS, THEIR SYNTHESIS AND USES THEREOF
  [FR] LIPIDES AMINÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS

  摘要：

  本发明提供了新的氨基脂质和一种方便的合成这些化合物的方法。这些（阳离子）氨基脂质作为转染剂具有良好的性能。该方法是一种经济多功能的两步合成方法，允许制备各种氨基脂质，从而导致转染剂组合库的组装。此外，本发明提供了含有上述氨基脂质的脂质粒子（脂质体）及其用于将生物活性剂输送到细胞中的用途。该发明还包括含有阳离子氨基脂质的脂质粒子作为药物的用途。

  公开号：

  WO2012167869A1
• 作为产物：
  描述：

  炔丙基脲 在 安息香双甲醚 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(2-(dimethylamino)ethyl)-4,5-bis(dodecylthio)pentanamide
  参考文献：
  名称：

  单尾类脂质增强其双尾配对物的转染活性

  摘要：

  阳离子脂质样分子（类脂）广泛用于体外和体内基因递送。迄今为止，几乎所有开发的类脂质都采用双尾或多尾结构进行转染。单尾类脂质在基因传递中效率低，因此很少考虑用于转染。到目前为止，还没有关于单尾类脂质与标准双尾类脂质结合使用对转染效率的贡献的详细研究。在这里，我们使用组合化学分别使用硫醇-炔和硫醇-烯点击化学来合成17个双尾和17个单尾类脂质。HEK 293T细胞用于通过荧光显微镜分析转染效率，并根据转染细胞的百分比进行计算。脂质体和脂质复合物的大小和ζ电位通过动态光散射（DLS）表征。共聚焦显微镜进一步检查了细胞内DNA的传递和运输。我们的研究表明，将单尾脂质与双尾脂质混合使用可增加脂质复合物的摄取以及细胞转染效率。

  DOI：

  10.1021/acscombsci.5b00117

文献信息

• [EN] AMINO LIPIDS, THEIR SYNTHESIS AND USES THEREOF<br/>[FR] LIPIDES AMINÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS
  申请人：KARLSRUHER INST TECHNOLOGIE

  公开号：WO2012167869A1

  公开（公告）日：2012-12-13

  The present invention provides new amino lipids and a convenient method for synthesising these compounds. These (cationic) amino lipids have good properties as transfection agents. The method is an economic versatile two step synthesis allowing the preparation of various amino lipids thus leading to the assembly of a combinatorial library of transfection agents. Moreover, the present invention provides lipid particles (liposomes) containing said amino lipids and their use for delivering bioactive agents into cells. The invention encompasses also the use of lipid particles containing the cationic amino lipids as medicament.

  本发明提供了新的氨基脂质和一种方便的合成这些化合物的方法。这些（阳离子）氨基脂质作为转染剂具有良好的性能。该方法是一种经济多功能的两步合成方法，允许制备各种氨基脂质，从而导致转染剂组合库的组装。此外，本发明提供了含有上述氨基脂质的脂质粒子（脂质体）及其用于将生物活性剂输送到细胞中的用途。该发明还包括含有阳离子氨基脂质的脂质粒子作为药物的用途。
• [EN] SYNTHESIS AND USE OF AMINO LIPIDS<br/>[FR] SYNTHÈSE ET UTILISATION DE LIPIDES AMINÉS
  申请人：INCELLA GMBH

  公开号：WO2016005318A1

  公开（公告）日：2016-01-14

  The present invention provides novel amino lipids and a method for synthesizing these compounds. According to the invention, the amino lipids have a structure of the following formula (I) wherein Z is either hydrogen or -X1 R1, R1 and R2 are the same or different and independently C6-C24 alkyl, C6-C24 alkenyl, C6-C24 alkynyl, or C6-C24 acyl, which can be optionally substituted with a C1-C6 hydrocarbyl group, X1 and X2 are the same or different, either S or S=O or S(=O)2, Y is either (II) or heterocycles of the formula (III) or (IV) wherein k and I are integers from 0 to 2, R3 and R4 are either the same or different and independently C1-C12 alkyl, C1-C12 alkenyl, or C1-C12 alkynyl, wherein alkyl, alkenyl or alkynyl may be optionally substituted with a C1-C6 hydrocarbyl group, or R3 and R4 optionally join to form, together with the nitrogen atom to which they are bound, an optionally substituted N-heterocyclic ring of 3 to 10 atoms comprising 1 to 7 nitrogen atoms, or R3 and R4 are the same or different alkyl amines; R5 and R6 are either absent or is hydrogen or C1-C12 alkyl to provide a quaternary amine, R7 is either hydrogen or C1-C12 alkyl, m is an integer from 1 to 12, n is an integer from 1 to 12, and p is an integer from 1 to 3, wherein preferably Y = N for p = 2 or 3.

  本发明提供了新型氨基脂质和合成这些化合物的方法。根据本发明，氨基脂质具有以下式（I）的结构，其中Z为氢或-X1 R1，R1和R2相同或不同，独立为C6-C24烷基，C6-C24烯基，C6-C24炔基或C6-C24酰基，可选择地取代为C1-C6烃基团，X1和X2相同或不同，为S或S=O或S(=O)2，Y为（II）或式（III）或（IV）的杂环，其中k和l为0至2的整数，R3和R4相同或不同，独立为C1-C12烷基，C1-C12烯基或C1-C12炔基，其中烷基，烯基或炔基可选择地取代为C1-C6烃基团，或R3和R4可选择地结合，与它们所结合的氮原子一起形成，可选择地取代的含有1至7个氮原子的3至10个原子的N-杂环，或R3和R4为相同或不同的烷基胺；R5和R6要么不存在，要么为氢或C1-C12烷基以提供季铵盐，R7要么为氢，要么为C1-C12烷基，m为1至12的整数，n为1至12的整数，p为1至3的整数，其中最好是Y = N，当p = 2或3时。
• AMINO LIPIDS, THEIR SYNTHESIS AND USES THEREOF
  申请人：Davidson Gary

  公开号：US20140187614A1

  公开（公告）日：2014-07-03

  The present invention provides new amino lipids and a convenient method for synthesising these compounds. These (cationic) amino lipids have good properties as transfection agents. The method is an economic versatile two step synthesis allowing the preparation of various amino lipids thus leading to the assembly of a combinatorial library of transfection agents. Moreover, the present invention provides lipid particles (liposomes) containing said amino lipids and their use for delivering bioactive agents into cells. The invention encompasses also the use of lipid particles containing the cationic amino lipids as medicament.

  本发明提供了新的氨基脂质和一种方便的合成这些化合物的方法。这些（阳离子）氨基脂质具有良好的转染剂特性。该方法是一种经济多功能的两步合成，允许制备各种氨基脂质，从而导致转染剂组合库的组装。此外，本发明提供了含有上述氨基脂质的脂质颗粒（脂质体）及其用于将生物活性剂递送到细胞内的用途。本发明还包括使用含有阳离子氨基脂质的脂质颗粒作为药物的用途。
• Synthesis and use of amino lipids
  申请人：Incella GmbH

  公开号：EP2966068A1

  公开（公告）日：2016-01-13

  The present invention provides novel amino lipids and a method for synthesizing these compounds.

  本发明提供了新型氨基脂和合成这些化合物的方法。
• SYNTHESIS AND USE OF AMINO LIPIDS
  申请人：INCELLA GMBH

  公开号：US20170204076A1

  公开（公告）日：2017-07-20

  The present invention provides novel amino lipids and a method for synthesizing these compounds. According to the invention, the amino lipids have a structure of the following formula: wherein Z is hydrogen or —X 1 R 1 , R 1 and R 2 are the same or different and independently C 6 -C 24 alkyl, C 6 -C 24 alkenyl, C 6 -C 24 alkynyl, or C 6 -C 24 acyl, X 1 and X 2 are the same or different, S, S═O or S(═O) 2 , Y is or heterocycles of the formula wherein k and l are integers from 0 to 2, R 3 and R 4 are either the same or different and independently C 1 -C 12 alkyl, C 1 -C 12 alkenyl, or C 1 -C 12 alkynyl, wherein alkyl, alkenyl or alkynyl may be optionally substituted with a C 1 -C 6 hydrocarbyl group, or R 3 and R 4 optionally join to form, together with the nitrogen atom to which they are bound, an optionally substituted N-heterocyclic ring of 3 to 10 atoms comprising 1 to 7 nitrogen atoms, or R 3 and R 4 are the same or different alkyl amines; R 5 and R 6 are absent or are hydrogen or C 1 -C 12 alkyl, R 7 is hydrogen or C 1 -C 12 alkyl, m is an integer from 1 to 12, n is an integer from 1 to 12, and p is an integer from 1 to 3, wherein Y═N for p=2 or 3.