5-formyluracil dimethylacetal | 59090-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-formyluracil dimethylacetal
• 英文别名: 5-(dimethoxymethyl)-1H-pyrimidine-2,4-dione
• CAS: 59090-36-7
• 化学式: C₇H₁₀N₂O₄
• mdl: MFCD00218487
• 分子量: 186.167
• InChiKey: LNJCHLMTMLCTDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 5-甲酰基尿嘧啶 在 Amberlite IR-120 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以91%的产率得到5-formyluracil dimethylacetal
  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

文献信息

• 5-(Dimethoxymethyl)-2^‘-Deoxyuridine:  A Novel Gem Diether Nucleoside with Anti-Orthopoxvirus Activity
  作者：Xuesen Fan、Xinying Zhang、Longhu Zhou、Kathy A. Keith、Earl R. Kern、Paul F. Torrence

  DOI：10.1021/jm0601710

  日期：2006.6.1

  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.