5-(2-methyl-1-propenyl)-2'-deoxyuridine | 86163-24-8

• 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: 5-(2-methyl-1-propenyl)-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-methylprop-1-enyl)pyrimidine-2,4-dione
• CAS: 86163-24-8
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: WZVFXMFAGVIUFP-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-methyl-1-propenyl)-2'-deoxyuridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5-(2-methyl-1-propyl)-2'-deoxyuridine
  参考文献：
  名称：

  Hassan, Mohamed Ezeldin, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 9, p. 1944 - 1948

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(2-methyl-allyl)-1H-pyrimidin-2-one 在 RhCl(PPh₃)3 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以61%的产率得到5-(2-methyl-1-propenyl)-2'-deoxyuridine
  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.
• Hassan, Mohamed Ezeldin, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 9, p. 1944 - 1948
  作者：Hassan, Mohamed Ezeldin

  DOI：——

  日期：——