5-乙炔基-1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮 | 156973-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-乙炔基-1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮
• 英文名称: 5-Ethynyl-1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
• CAS: 156973-14-7
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: WAXIUEZBEULFPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-乙炔基-1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮 在 copper(l) iodide 、 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 15.0h， 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
• 作为产物：
  描述：

  1-(2-羟基乙氧基甲基)-5-碘-1H-嘧啶-2,4-二酮 、 三甲基乙炔基硅 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 4.0h， 生成 5-乙炔基-1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮
  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

文献信息

• Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl] Analogues of Antiviral Furo- and Pyrrolo[2,3-<i>d</i>]pyrimidine Nucleosides
  作者：Zlatko Janeba、Jan Balzarini、Graciela Andrei、Robert Snoeck、Erik De Clercq、Morris J. Robins

  DOI：10.1021/jm050291s

  日期：2005.7.1

  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.