3'-O-acetyl-5-ethyl-4'-thio-2'-deoxyuridine | 175471-00-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-O-acetyl-5-ethyl-4'-thio-2'-deoxyuridine
• 英文别名: 3'-O-acetyl-4'-thio-5-ethyl-2'-deoxyuridine；[(2R,3S,5R)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)thiolan-3-yl] acetate
• CAS: 175471-00-8
• 化学式: C₁₃H₁₈N₂O₅S
• 分子量: 314.362
• InChiKey: GDVZRPJTGQFMGJ-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5-ethyl-4'-thio-2'-deoxyuridine 在 亚磷酸 、 氨 作用下， 以63%的产率得到4'-thio-5-ethyl-2'-deoxyuridine 5'-phosphonate
  参考文献：
  名称：

  摘要：

  A number of new 5'-phosphonate derivatives of 4'-thio-5-ethyl-2'-deoxyuridine (TEDU) were synthesized. These compounds displayed a low cytotoxicity and, except for TEDU 5'-fluorophosphate, antiherpes activity similar to that of 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir) and 9-(1,3-dihydroxy-2-propoxymethyl)guanine (pencyclovir). 5'-Ethoxycarbonylphosphonate and 5'-aminocarbonylphosphonate of TEDU were also found to suppress the reproduction of herpes simplex type I virus, which is resistant to acyclovir.

  DOI：

  10.1023/a:1020476212905
• 作为产物：
  描述：

  4'-硫代-5-乙基-2'-脱氧尿苷 在 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 44.0h， 生成 3'-O-acetyl-5-ethyl-4'-thio-2'-deoxyuridine
  参考文献：
  名称：

  Some Reactions of 4′-Thionucleosides and Their Sulfones

  摘要：

  We report interesting and novel reactions of 4'-thionucleosides and their sulfone derivatives when a good leaving group is present in the 5'-position. The results have important implications for the phosphorylation of these nucleoside analogues by standard chemical procedures. Possible mechanisms for these reactions are discussed.

  DOI：

  10.1080/07328319608002376