N-[12-(2,3-dihydroxypropoxy)dodecyl]-2,2,2-trifluoroacetamide | 1251757-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: N-[12-(2,3-dihydroxypropoxy)dodecyl]-2,2,2-trifluoroacetamide
• CAS: 1251757-45-5
• 化学式: C₁₇H₃₂F₃NO₄
• 分子量: 371.441
• InChiKey: ZZDPVLWVZYTGJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[12-(2,3-dihydroxypropoxy)dodecyl]-2,2,2-trifluoroacetamide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以58%的产率得到N-[12-[3-[bis(4-methoxyphenyl)(phenyl)methoxy]-2-hydroxypropoxy]dodecyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies

  摘要：

  Novel lipid derivatives carrying amino and triazolyl groups were efficiently synthesized and covalently anchored at the 3'-termini of oligonucleondes The desired amino-lipid conjugates were fully characterized by reversed-phase HPLC and MALDI-TOF mass spectrometry The methodology was applied in the synthesis of lipid-siRNA designed to inhibit necrosis factor (TNF-alpha) in order to obtain siRNAs with anti-inflammatory properties The siRNA duplex carrying amino-lipids at the 3'-end of the passenger strand has inhibitory properties similar to those of unmodified RNA duplexes in HeLa cells. indicating that the new lipid derivatives ate compatible with the RNA interference machinery

  DOI：

  10.1021/jo101143j
• 作为产物：
  描述：

  三氟乙酸乙酯 、 tert-butyl 12-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]dodecylcarbamate 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以87%的产率得到N-[12-(2,3-dihydroxypropoxy)dodecyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies

  摘要：

  Novel lipid derivatives carrying amino and triazolyl groups were efficiently synthesized and covalently anchored at the 3'-termini of oligonucleondes The desired amino-lipid conjugates were fully characterized by reversed-phase HPLC and MALDI-TOF mass spectrometry The methodology was applied in the synthesis of lipid-siRNA designed to inhibit necrosis factor (TNF-alpha) in order to obtain siRNAs with anti-inflammatory properties The siRNA duplex carrying amino-lipids at the 3'-end of the passenger strand has inhibitory properties similar to those of unmodified RNA duplexes in HeLa cells. indicating that the new lipid derivatives ate compatible with the RNA interference machinery

  DOI：

  10.1021/jo101143j

文献信息

• [EN] LIPOPHILIC DERIVATIVES OF NUCLEIC ACIDS<br/>[ES] DERIVADOS LIPOFÍLICOS DE ÁCIDOS NUCLEICOS<br/>[FR] DÉRIVÉS LIPOPHILES D'ACIDES NUCLÉIQUES
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2011135138A1

  公开（公告）日：2011-11-03

  En esta invención se describen nuevos derivados del pARNi. El pARNi modificado según la invención mejora su entrada en las células y su estabilidad a la degradación por nucleasas, aumentando la capacidad inhibitoria de los pARNi. Estos nuevos compuestos contienen lípidos unidos a una molécula puente presente en el extremo terminal del dúplex de pARNi mediante enlaces tipo éter. También se describe la síntesis de dichos compuestos.