3',5'-di-O-acetyl-5-formyl-2'-deoxyuridine ethylene acetal | 890406-42-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-di-O-acetyl-5-formyl-2'-deoxyuridine ethylene acetal
• 英文别名: [(2R,3S,5R)-3-acetoxy-5-[5-(1,3-dioxolan-2-yl)-2,4-dioxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate；[(2R,3S,5R)-3-acetyloxy-5-[5-(1,3-dioxolan-2-yl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 890406-42-5
• 化学式: C₁₆H₂₀N₂O₉
• 分子量: 384.343
• InChiKey: YMUNJQHMHYUSGF-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-5-formyl-2'-deoxyuridine ethylene acetal 在 氨 作用下， 以 甲醇 为溶剂， 生成 5-(1,3-dioxolan-2-yl)-1-((2R,4R,5R)-tetrahydro-4-hydroxy-5-(hydroxymethyl)furan-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  5-(Dimethoxymethyl)-2^‘-Deoxyuridine:  A Novel Gem Diether Nucleoside with Anti-Orthopoxvirus Activity

  摘要：

  To provide potential new leads for the treatment of orthopoxvirus infections, the 5-position of the pyrimidine nucleosides have been modified with a gem diether moiety to yield the following new nucleosides: 5-(dimethoxymethyl)-2-deoxyuridine (2b), 5-(diethoxymethyl)-2-deoxyuridine (3b), 5-formyl-2-deoxyuridine ethylene acetal (4b), and 5formyl-2-deoxyuridine propylene acetal (5b). These were evaluated in human foreskin fibroblast cells challenged with the vaccinia virus or cowpox virus. Of the four gem diether nucleosides, only the dimethyl gem diether congener showed significant antiviral activity against both viruses. This antiviral activity did not appear to be related to the decomposition to the 5-formyl-2-deoxyuridine, which was itself devoid of anti-orthopoxvirus activity in these assays. Moreover, at the pH of the in vitro assays, 2b was very stable with a decomposition (to aldehyde) half-life of > 15 d. The anti-orthopoxvirus activity of pyrimidine may be favored by the introduction of hydrophilic moieties to the 5- position side chain.

  DOI：

  10.1021/jm0601710
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 2,6-二甲基吡啶 、 dipotassium peroxodisulfate 、 Amberlite IR-120 、 copper(II) sulfate 作用下， 以 乙腈 、 苯 为溶剂， 反应 3.0h， 生成 3',5'-di-O-acetyl-5-formyl-2'-deoxyuridine ethylene acetal
  参考文献：
  名称：

  5-(Dimethoxymethyl)-2^‘-Deoxyuridine:  A Novel Gem Diether Nucleoside with Anti-Orthopoxvirus Activity

  摘要：

  To provide potential new leads for the treatment of orthopoxvirus infections, the 5-position of the pyrimidine nucleosides have been modified with a gem diether moiety to yield the following new nucleosides: 5-(dimethoxymethyl)-2-deoxyuridine (2b), 5-(diethoxymethyl)-2-deoxyuridine (3b), 5-formyl-2-deoxyuridine ethylene acetal (4b), and 5formyl-2-deoxyuridine propylene acetal (5b). These were evaluated in human foreskin fibroblast cells challenged with the vaccinia virus or cowpox virus. Of the four gem diether nucleosides, only the dimethyl gem diether congener showed significant antiviral activity against both viruses. This antiviral activity did not appear to be related to the decomposition to the 5-formyl-2-deoxyuridine, which was itself devoid of anti-orthopoxvirus activity in these assays. Moreover, at the pH of the in vitro assays, 2b was very stable with a decomposition (to aldehyde) half-life of > 15 d. The anti-orthopoxvirus activity of pyrimidine may be favored by the introduction of hydrophilic moieties to the 5- position side chain.

  DOI：

  10.1021/jm0601710