Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-iodo-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester | 1053705-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-iodo-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,5S)-3-acetyloxy-5-[5-iodo-2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxan-2-yl]methyl acetate
• CAS: 1053705-73-9
• 化学式: C₁₆H₁₈IN₅O₆
• 分子量: 503.253
• InChiKey: LJWINVKCFOAXTF-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-iodo-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester 在 ammonium hydroxide 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 生成 1,5-anhydro-2,3-dideoxy-2-(5-iodocytosin-1-yl)-D-arabino-hexitol
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure Analysis of a Series of New 1,5-Anhydrohexitol Nucleosides

  摘要：

  In view of the selective anti-HSV activity of 1,5-anhydro-2,3-dideoxy-2-(5-iodouracil-1-yl)-D-arabino-hexitol,(1) a series of novel 1,5-anhydrohexitol nucleosides were synthesized and evaluated for their inhibitory activity against several viruses. The 5-iodouracil 3 and the 5-ethyluracil 4 derivatives are highly selective TK-dependent inhibitors of HSV-1 and HSV-2. Broad anti-herpes virus activity was noticed for 5-fluorocytosine 6 and 2,6-diaminopurine 10 analogues. From a transport study of 3, using the thymidine influx competition method, one can conclude that intracellular uptake of this compound most probably occurs by passive diffusion. X-ray analysis of compounds 3 and 9 showed that the heterocyclic base of 1,5-anhydrohexitol pyrimidine and purine is placed in the axial position and that the sugar ring adopts a slightly distorted chair conformation.

  DOI：

  10.1021/jm00005a010
• 作为产物：
  描述：

  3-Benzoyl-5-iodo-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 氨 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 79.0h， 生成 Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-iodo-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure Analysis of a Series of New 1,5-Anhydrohexitol Nucleosides

  摘要：

  In view of the selective anti-HSV activity of 1,5-anhydro-2,3-dideoxy-2-(5-iodouracil-1-yl)-D-arabino-hexitol,(1) a series of novel 1,5-anhydrohexitol nucleosides were synthesized and evaluated for their inhibitory activity against several viruses. The 5-iodouracil 3 and the 5-ethyluracil 4 derivatives are highly selective TK-dependent inhibitors of HSV-1 and HSV-2. Broad anti-herpes virus activity was noticed for 5-fluorocytosine 6 and 2,6-diaminopurine 10 analogues. From a transport study of 3, using the thymidine influx competition method, one can conclude that intracellular uptake of this compound most probably occurs by passive diffusion. X-ray analysis of compounds 3 and 9 showed that the heterocyclic base of 1,5-anhydrohexitol pyrimidine and purine is placed in the axial position and that the sugar ring adopts a slightly distorted chair conformation.

  DOI：

  10.1021/jm00005a010