Acetic acid 2-{(2-acetoxy-benzyloxy)-[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethoxy]-phosphoryloxymethyl}-phenyl ester

• 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: Acetic acid 2-{(2-acetoxy-benzyloxy)-[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethoxy]-phosphoryloxymethyl}-phenyl ester
• 英文别名: [2-[[(2-acetoxyphenyl)methoxy-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]oxymethyl]phenyl] acetate；[2-[[(2-acetyloxyphenyl)methoxy-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]oxymethyl]phenyl] acetate
• 化学式: C₂₈H₂₉N₂O₁₁P
• 分子量: 600.519
• InChiKey: BCSIKXKBBNDZFI-JYFHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-{(2-acetoxy-benzyloxy)-[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethoxy]-phosphoryloxymethyl}-phenyl ester 在 PBS buffer 作用下， 以 水 为溶剂， 生成 3'-deoxy-2',3'-didehydro-5'-O-dihydroxyphosphoryl thymidine
  参考文献：
  名称：

  Study of Different Substituted Cyclic and Acyclic Benzylpronucleotides of d4T Relative to Their Hydrolytic Stability and Antiviral Activity

  摘要：

  CycloSal-d4TMP and two different bis(benzyl) phosphate triesters of the anti-virally active nucleoside analog d4T were studied with regard to their chemical hydrolysis behavior at pH 7.3, in CEM/0 cell extracts, and their anti-HIV activity. In contrast to triesters 2-4, bis-(o-AB)-d4TMP 1 was found to be chemically exquisitely stable. All compounds led to the formation of d4TMP in cell extracts and all triesters achieved the TK-bypass.

  DOI：

  10.1081/ncn-120022636