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

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: methyl 2-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxy-phosphoryl]oxyacetate
• 英文别名: methyl 2-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxyphosphoryl]oxyacetate
• 化学式: C₁₉H₂₁N₂O₉P
• 分子量: 452.357
• InChiKey: PSKOXBLIWSKVAO-XPFOVHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  司他夫定 、 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以80%的产率得到methyl 2-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxy-phosphoryl]oxyacetate
  参考文献：
  名称：

  Lactate cannot substitute for alanine in D4T-based anti-HIV nucleotide prodrugs-despite efficient esterase-mediated hydrolysis

  摘要：

  As part of our on-going effort to deliver masked phosphates of antiviral nucleosides inside living cells we have previously discovered that amino acid-derived phosphoramidates are particularly effective. Here we report that lactate analogues, with a simple change of bridging nitrogen for oxygen, are virtually inactive as antiviral agents and apparently do not achieve intracellular nucleoside phosphate delivery. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00530-7