methyl (E)-3-[4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-5-yl]but-2-enoate | 86163-22-6

• 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: methyl (E)-3-[4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-5-yl]but-2-enoate
• 英文别名: methyl (E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]but-2-enoate
• CAS: 86163-22-6
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: YFZNOOMGFGYWNL-JONPOOTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-5-yl]but-2-enoate 在 sodium hydroxide 、 N-氯代丁二酰亚胺 作用下， 生成 5-((E)-2-Chloro-1-methyl-vinyl)-4-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009
• 作为产物：
  描述：

  巴豆酸甲酯 、 5-(chloromercuri)-2'-deoxyuridine 在 lithium tetrachloropalladate 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以21%的产率得到methyl (E)-3-[4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-5-yl]but-2-enoate
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009

文献信息

• Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity
  作者：John Goodchild、Roderick A. Porter、Robert H. Raper、Iain S. Sim、Roger M. Upton、Julie Viney、Harry J. Wadsworth

  DOI：10.1021/jm00363a009

  日期：1983.9

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.