Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester | 1055028-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,5S)-3-acetyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 1055028-13-1
• 化学式: C₁₄H₁₇FN₂O₇
• 分子量: 344.297
• InChiKey: CPENIMIPKGUYOU-ZMLRMANQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 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-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-3-yl ester 在 吡啶 、 ammonium hydroxide 、 氨 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 76.0h， 生成 1,5-anhydro-2,3-dideoxy-2-(5-fluorocytosin-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：

  1,5-脱水-3-脱氧-4,6-O-(苯基亚甲基)-D-核-己糖醇 在 吡啶 、 氨 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(5-fluoro-2,4-dioxo-3,4-dihydro-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