O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) N-(2-ethoxycarbonylethyl)phosphoramidate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) N-(2-ethoxycarbonylethyl)phosphoramidate
• 英文别名: ethyl 3-[[[(2R,3R,5S)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate；ethyl 3-[[[(2R,3R,5S)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]amino]propanoate
• 化学式: C₂₅H₃₄N₁₁O₁₁P
• 分子量: 695.586
• InChiKey: QIYLGOGYHYXPTE-GSGZDVGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  220
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  齐多夫定 在 pyridinium phosphonate 、 吡啶盐酸盐 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 四氯化碳 、 三乙胺 为溶剂， 反应 1.17h， 生成 O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) N-(2-ethoxycarbonylethyl)phosphoramidate
  参考文献：
  名称：

  Synthesis and Anti-Retroviral Activity ofO,O′-BIS(3′-Azido-2′,3′-Dideoxythymidin-5′-yl) Phosphoramidate Derivatives

  摘要：

  A simple and efficient protocol for the preparation of various symmetrical dinucleoside phosphoramidates derived from AZT, is presented. It consists of the phosphonylation of AZT with phosphonic acid in the presence of DCC to produce the symmetrical H-phosphonate diester, followed by its oxidative conversion to various phosphoramidate analogues. The synthesized compounds were evaluated for their anti-HIV activity in different cell cultures.

  DOI：

  10.1080/07328319908044884

文献信息

• Synthesis and Anti-Retroviral Activity of<i>O,O′-BIS</i>(3′-Azido-2′,3′-Dideoxythymidin-5′-yl) Phosphoramidate Derivatives
  作者：Inger Kers、Jacek Stawiński、Jean-Luc Girardet、Jean-Louis Imbach、Christian Perigaud、Gilles Gosselin、Anne-Marie Aubertin

  DOI：10.1080/07328319908044884

  日期：1999.10

  A simple and efficient protocol for the preparation of various symmetrical dinucleoside phosphoramidates derived from AZT, is presented. It consists of the phosphonylation of AZT with phosphonic acid in the presence of DCC to produce the symmetrical H-phosphonate diester, followed by its oxidative conversion to various phosphoramidate analogues. The synthesized compounds were evaluated for their anti-HIV activity in different cell cultures.