benzyl (2S)-2-[[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate

• 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: benzyl (2S)-2-[[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate
• 英文别名: benzyl (2S)-2-[[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
• 化学式: C₂₆H₂₈N₃O₈P
• 分子量: 541.497
• InChiKey: LBODADFUSMWQAZ-CFPMFFHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  司他夫定 、 phenyl(benzyloxy-L-alaninyl)phosphorochloridate 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl (2S)-2-[[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate
  参考文献：
  名称：

  Phosphoramidate derivatives of d4T with improved anti-HIV efficacy retain full activity in thymidine kinase-deficient cells

  摘要：

  New phosphate derivatives of the anti-HIV nucleoside analogue d4T were prepared as potential membrane-soluble pro-drugs of the bio-active free nucleotide. Some of the derivatives appear to have enhanced antiviral efficacy relative to the parent nucleoside analogue. Moreover, the derivatives appear to by-pass the dependence of the nucleoside on thymidine kinase-mediated activation, retaining full activity in thymidine kinase-deficient cells. The new analogues show particular promise for further pre-clinical development. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00195-3

文献信息

• Phosphoramidate derivatives of d4T with improved anti-HIV efficacy retain full activity in thymidine kinase-deficient cells
  作者：Christopher McGuigan、Dominique Cahard、Hendrika M. Sheeka、Erik De Clercq、Jan Balzarini

  DOI：10.1016/0960-894x(96)00195-3

  日期：1996.5

  New phosphate derivatives of the anti-HIV nucleoside analogue d4T were prepared as potential membrane-soluble pro-drugs of the bio-active free nucleotide. Some of the derivatives appear to have enhanced antiviral efficacy relative to the parent nucleoside analogue. Moreover, the derivatives appear to by-pass the dependence of the nucleoside on thymidine kinase-mediated activation, retaining full activity in thymidine kinase-deficient cells. The new analogues show particular promise for further pre-clinical development. (C) 1996 Elsevier Science Ltd