N-(2-octadecanoylaminoethyl)-N-(thymin-1-ylacetyl)glycine methyl ester | 625442-92-4

• 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-(2-octadecanoylaminoethyl)-N-(thymin-1-ylacetyl)glycine methyl ester
• 英文别名: Methyl 2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-(octadecanoylamino)ethyl]amino]acetate
• CAS: 625442-92-4
• 化学式: C₃₀H₅₂N₄O₆
• 分子量: 564.766
• InChiKey: FKCUUOWDGRWORJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-octadecanoylaminoethyl)-N-(thymin-1-ylacetyl)glycine methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以97%的产率得到N-(2-octadecanoylaminoethyl)-N-(thymin-1-ylacetyl)glycine
  参考文献：
  名称：

  Lipophilic peptide nucleic acids containing a 1,3-diyne function: synthesis, characterization and production of derived polydiacetylene liposomes

  摘要：

  Adenine-, cytosine- and thymine-containing peptide nucleic acid (PNA) monomers have been synthesized in which either diacetylenic or stearoyl moieties are attached to the N-or C-terminus; the diacetylenic group is embedded within a long hydrocarbon chain. A range of analogous lipophilic functionalized PNA oligomers have been prepared using either solid phase synthesis or a post-synthetic solution phase procedure following cleavage of the PNA oligomer from the solid Support. Selected functionalized PNA monomers and oligomers have been incorporated into liposomal polydiacetylenes and characterized by UV-vis absorption spectroscopy. Preliminary investigations show that blue PDA-liposomes containing thymine-based PNAs can be formed and that production of liposomes with other PNA systems are viable. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.021
• 作为产物：
  描述：

  N-(2-aminoethyl)glycine methyl ester dihydrochloride 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-octadecanoylaminoethyl)-N-(thymin-1-ylacetyl)glycine methyl ester
  参考文献：
  名称：

  Synthesis and polymerisation of lipophilic peptide nucleic acids derived from stearic acid and pentacosa-10,12-diynoic acid

  摘要：

  The adenine, cytosine and thymine peptide nucleic acid (PNA) monomers and PNA T-10 oligomers bearing either a diacetylenic or stearoyl moiety at the N- or C-terminus have been successfully prepared. The resulting thymine monomeric and T-10-mer derivatives have been subsequently incorporated into polydiacetylene-containing liposomes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.047

文献信息

• Investigation of Novel Lipid-Functionalized PNA Monomers as Potential HIV-1 Non-Nucleoside Reverse Transcriptase and/or Integrase Inhibitors
  作者：Michael G. Thomas、Giovanni Maga、Jean-François Mouscadet、Nicola M. Howarth

  DOI：10.1080/15257770701513414

  日期：2007.11.26

  A range of novel N-terminal lipid-functionalized peptide nucleic acid (PNA) monomers have been prepared and their abilities to inhibit HIV-1 reverse transcriptase and integrase have been examined.