N,N-dioctadecyl-3-sulfanylpropanamide | 153626-23-4

• 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,N-dioctadecyl-3-sulfanylpropanamide
• CAS: 153626-23-4
• 化学式: C₃₉H₇₉NOS
• 分子量: 610.128
• InChiKey: PRDCXPNHCRIUJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.6
• 重原子数：
  42
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-acrylamidoethyl)carbamate 、 N,N-dioctadecyl-3-sulfanylpropanamide 在 偶氮二异丁腈 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (2-{4,6-Bis-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-2-[2-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-3-(2-dioctadecylcarbamoyl-ethylsulfanyl)-propyl]-hexanoylamino}-ethyl)-carbamic acid tert-butyl ester 、 {2-[2-[2,4-Bis-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-butyl]-4,6-bis-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-7-(2-dioctadecylcarbamoyl-ethylsulfanyl)-heptanoylamino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Lipopolycationic Telomers for Gene Transfer: Synthesis and Evaluation of Their in Vitro Transfection Efficiency

  摘要：

  We report on the synthesis of a series of lipopolyamine telomers I-14,n, I-18,n, and II-18,n and on their in vitro gene-transfer capability. Their structure consists of a polyamine polar moiety, including n primary amine functions (from 1 to 70), connected to a hydrophobic moiety, including two hydrocarbon C14 or C18 chains, through a mercaptopropanoyl or mercaptoglyceryl unit and an amide or ether function. They were obtained by telomerization of N-(2-[(BOC)aminoethyl]})acrylamide with N,N-ditetradecyl- and N,N-dioctadecylpropanamide-3-thiol and rac-1,2-dioctadecyloxypropane-3-thiol, respectively, then BOC deprotection. For NIP ratios (N = number of telomer amine equivalents; P = number of DNA phosphates) from 0.8 to 10, these lipopolyamines condensed DNA, with or without the use of DOPE, forming lipopolyplexes or teloplexes of mean sizes less than zoo nm. Some trends, structure-activity and structure-toxicity relationships, were established to achieve both highest in vitro transfection levels and cell viability. Thus, DNA formulations based on telomers I-14,20 and I-18,20 and for NIP ratios lower than 5 led to the most efficient teloplex formulations for plasmid delivery to lung epithelial A549 cells.

  DOI：

  10.1021/jm9911579
• 作为产物：
  描述：

  N,N,N',N'-tetraoctadecyl-3,3'-(disulfanediyl)dipropanamide 在 溶剂黄146 、 锌 作用下， 反应 3.0h， 以82%的产率得到N,N-dioctadecyl-3-sulfanylpropanamide
  参考文献：
  名称：

  Lipopolycationic Telomers for Gene Transfer: Synthesis and Evaluation of Their in Vitro Transfection Efficiency

  摘要：

  We report on the synthesis of a series of lipopolyamine telomers I-14,n, I-18,n, and II-18,n and on their in vitro gene-transfer capability. Their structure consists of a polyamine polar moiety, including n primary amine functions (from 1 to 70), connected to a hydrophobic moiety, including two hydrocarbon C14 or C18 chains, through a mercaptopropanoyl or mercaptoglyceryl unit and an amide or ether function. They were obtained by telomerization of N-(2-[(BOC)aminoethyl]})acrylamide with N,N-ditetradecyl- and N,N-dioctadecylpropanamide-3-thiol and rac-1,2-dioctadecyloxypropane-3-thiol, respectively, then BOC deprotection. For NIP ratios (N = number of telomer amine equivalents; P = number of DNA phosphates) from 0.8 to 10, these lipopolyamines condensed DNA, with or without the use of DOPE, forming lipopolyplexes or teloplexes of mean sizes less than zoo nm. Some trends, structure-activity and structure-toxicity relationships, were established to achieve both highest in vitro transfection levels and cell viability. Thus, DNA formulations based on telomers I-14,20 and I-18,20 and for NIP ratios lower than 5 led to the most efficient teloplex formulations for plasmid delivery to lung epithelial A549 cells.

  DOI：

  10.1021/jm9911579