2-[4-[1-[12-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]dodecyl]-1H-1,2,3-triazol-4-yl]butyl]isoindoline-1,3-dione | 1251757-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[4-[1-[12-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]dodecyl]-1H-1,2,3-triazol-4-yl]butyl]isoindoline-1,3-dione
• 英文别名: 2-[4-[1-[12-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy]dodecyl]triazol-4-yl]butyl]isoindole-1,3-dione
• CAS: 1251757-48-8
• 化学式: C₃₂H₄₈N₄O₅
• 分子量: 568.757
• InChiKey: JKBXVFKFIWKWNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[4-[1-[12-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]dodecyl]-1H-1,2,3-triazol-4-yl]butyl]isoindoline-1,3-dione 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到2-[4-[1-[12-(2,3-dihydroxypropoxy)dodecyl]-1H-1,2,3-triazol-4-yl]butyl]isoindoline-1,3-dione
  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：

  N-(5-己炔基)酞酰亚胺 、 4-[(12-azidododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以89%的产率得到2-[4-[1-[12-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]dodecyl]-1H-1,2,3-triazol-4-yl]butyl]isoindoline-1,3-dione
  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

• Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies
  作者：Santiago Grijalvo、Sandra M. Ocampo、José C. Perales、Ramon Eritja

  DOI：10.1021/jo101143j

  日期：2010.10.15

  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