3-(2-Hydroxyethoxymethyl)-6-undecyl-furo[2,3-d]pyrimidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-(2-Hydroxyethoxymethyl)-6-undecyl-furo[2,3-d]pyrimidin-2-one
• 英文别名: 3-(2-hydroxyethoxymethyl)-6-undecylfuro[2,3-d]pyrimidin-2-one
• 化学式: C₂₀H₃₂N₂O₄
• 分子量: 364.485
• InChiKey: COXXGHODOAKGER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Hydroxyethoxymethyl)-6-undecyl-furo[2,3-d]pyrimidin-2-one 在 氨 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以53%的产率得到3-(2-hydroxyethoxymethyl)-6-undecyl-7H-pyrrolo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl] Analogues of Antiviral Furo- and Pyrrolo[2,3-d]pyrimidine Nucleosides

  摘要：

  The remarkably potent and specific activity against varicella-zoster virus (VZV) shown by 2'deoxymicleosides of furo[2,3-d]pyrimidin-2(3H)-one and related ring systems is dependent on key structural features including the length and nature of the side-chain at C6 and the structure and stereochemistry of the sugar moiety at N3. Removal of the X-hydroxyl group from potent anti-VZV 2'-deoxynucleosides results in loss of the VZV activity, but such 2',3'-dideoxynucleoside analogues have shown anti-HCMV activity. We now report acyclic analogues with comparable side-chains at C6, but with the sugar moiety at N3 replaced with the (2-hydroxyethoxy)methyl group (present in the antiherpes drug acyclovir). Examples of both furo[2,3, d]-and pyrrolo[2,3-d]pyrimidin-2(3H)-one acyclic analogues were prepared and evaluated in a number of virus infected cells and in tumor cell cultures. Certain of the long-chain analogues showed activity against VZV and HCMV. No significant activity against other DNA and RNA virus replication or against tumor cell proliferation was observed.

  DOI：

  10.1021/jm050291s
• 作为产物：
  描述：

  1-十三炔 、 1-(2-羟基乙氧基甲基)-5-碘-1H-嘧啶-2,4-二酮 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以68%的产率得到3-(2-Hydroxyethoxymethyl)-6-undecyl-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl] Analogues of Antiviral Furo- and Pyrrolo[2,3-d]pyrimidine Nucleosides

  摘要：

  The remarkably potent and specific activity against varicella-zoster virus (VZV) shown by 2'deoxymicleosides of furo[2,3-d]pyrimidin-2(3H)-one and related ring systems is dependent on key structural features including the length and nature of the side-chain at C6 and the structure and stereochemistry of the sugar moiety at N3. Removal of the X-hydroxyl group from potent anti-VZV 2'-deoxynucleosides results in loss of the VZV activity, but such 2',3'-dideoxynucleoside analogues have shown anti-HCMV activity. We now report acyclic analogues with comparable side-chains at C6, but with the sugar moiety at N3 replaced with the (2-hydroxyethoxy)methyl group (present in the antiherpes drug acyclovir). Examples of both furo[2,3, d]-and pyrrolo[2,3-d]pyrimidin-2(3H)-one acyclic analogues were prepared and evaluated in a number of virus infected cells and in tumor cell cultures. Certain of the long-chain analogues showed activity against VZV and HCMV. No significant activity against other DNA and RNA virus replication or against tumor cell proliferation was observed.

  DOI：

  10.1021/jm050291s