5-(uracil-5-ylmethylene)-3-phenyl-2-thiohydantoin | 157365-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(uracil-5-ylmethylene)-3-phenyl-2-thiohydantoin
• 英文别名: 5-[(5-oxo-1-phenyl-2-sulfanylideneimidazolidin-4-ylidene)methyl]-1H-pyrimidine-2,4-dione
• CAS: 157365-67-8
• 化学式: C₁₄H₁₀N₄O₃S
• 分子量: 314.324
• InChiKey: ZRPPARRXTAUGNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(uracil-5-ylmethylene)-3-phenyl-2-thiohydantoin 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-<1-(2-deoxy-α-D-erythro-pentofuranosyl)uracil-5-ylmethylene>-3-phenyl-2-thiohydantoin
  参考文献：
  名称：

  Synthesis and evaluation of antiviral activity of 2?-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position

  摘要：

  1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) was synthesized from 5-formyluracil and an appropriate methyl glycoside and condensed with 2-thiohydantoin (5a) and its corresponding 3-phenyl derivative 5b to give 5-[1-(2-deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)uracil-5-ylmethylene]-2-thiohydantoins 7a and 7b, respectively, in 65-70% yield. They were deprotected with sodium methoxide in methanol to give both anomers of the free nucleosides. In a different route 5-formyluracil (1) was condensed with 5b and subsequently with an appropriate methyl glycoside to give 7b.

  DOI：

  10.1007/bf00811853
• 作为产物：
  描述：

  5-甲酰基尿嘧啶 、 苯基乙内酰脲-甘氨酸 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以74%的产率得到5-(uracil-5-ylmethylene)-3-phenyl-2-thiohydantoin
  参考文献：
  名称：

  Synthesis and evaluation of antiviral activity of 2?-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position

  摘要：

  1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) was synthesized from 5-formyluracil and an appropriate methyl glycoside and condensed with 2-thiohydantoin (5a) and its corresponding 3-phenyl derivative 5b to give 5-[1-(2-deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)uracil-5-ylmethylene]-2-thiohydantoins 7a and 7b, respectively, in 65-70% yield. They were deprotected with sodium methoxide in methanol to give both anomers of the free nucleosides. In a different route 5-formyluracil (1) was condensed with 5b and subsequently with an appropriate methyl glycoside to give 7b.

  DOI：

  10.1007/bf00811853