6-bromo-3-[(2-hydroxyethoxy)methyl]furo[2,3-d]pyrimidin-2-one | 862462-85-9

• 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: 6-bromo-3-[(2-hydroxyethoxy)methyl]furo[2,3-d]pyrimidin-2-one
• 英文别名: 6-Bromo-3-(2-hydroxyethoxymethyl)furo[2,3-d]pyrimidin-2-one
• CAS: 862462-85-9
• 化学式: C₉H₉BrN₂O₄
• 分子量: 289.085
• InChiKey: LYBJOVKPAFOXEB-UHFFFAOYSA-N

物化性质

• 熔点：
  135-145 °C
• 沸点：
  432.1±55.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  6-bromo-3-[(2-hydroxyethoxy)methyl]furo[2,3-d]pyrimidin-2-one 、 1-壬炔 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 10.0h， 以51%的产率得到3-(2-Hydroxyethoxymethyl)-6-non-1-ynyl-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
• 作为产物：
  描述：

  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 、 溴 、 potassium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 6-bromo-3-[(2-hydroxyethoxy)methyl]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