4'-thio-5-ethyl-2'-deoxyuridine 5'-ethoxycarbonylphosphonate | 251442-83-8

• 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: 4'-thio-5-ethyl-2'-deoxyuridine 5'-ethoxycarbonylphosphonate
• 英文别名: ethoxycarbonyl-[[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrothiophen-2-yl]methoxy]phosphinic acid；ethoxycarbonyl-[[(2R,3S,5R)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-3-hydroxythiolan-2-yl]methoxy]phosphinic acid
• CAS: 251442-83-8
• 化学式: C₁₄H₂₁N₂O₈PS
• 分子量: 408.369
• InChiKey: IPAQUOWAHBITBY-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4'-thio-5-ethyl-2'-deoxyuridine 5'-ethoxycarbonylphosphonate 在 ammonium hydroxide 作用下， 以85%的产率得到4'-thio-5-ethyl-2'-deoxyuridine 5'-aminocarbonylphosphonate
  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：

  ethoxycarbonylphosphonic acid 、 4'-硫代-5-乙基-2'-脱氧尿苷 在 N,N'-二环己基碳二亚胺 作用下， 以57%的产率得到4'-thio-5-ethyl-2'-deoxyuridine 5'-ethoxycarbonylphosphonate
  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

文献信息

• ——
  作者：L. A. Aleksandrova、V. L. Andronova、I. L. Karpenko、Yu. S. Skoblov、A. Adani、G. A. Galegov

  DOI：10.1023/a:1020476212905

  日期：——

  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.