1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(trifluoromethyl)uracil | 84500-34-5

• 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: 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(trifluoromethyl)uracil
• 英文别名: [(2R,3R,4S,5R)-3,4-diacetyloxy-5-[2,4-dioxo-5-(trifluoromethyl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 84500-34-5
• 化学式: C₁₆H₁₇F₃N₂O₉
• 分子量: 438.314
• InChiKey: RLCSLIOGASUNBC-NRWUCQMLSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(trifluoromethyl)uracil 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以80%的产率得到5-Trifluormethyl-1β-D-arabinofuranosyluracil
  参考文献：
  名称：

  Synthesis and biological activity of 5-(trifluoromethyl)- and 5-(pentafluoroethyl)pyrimidine nucleoside analogs

  摘要：

  Various 5-substituted perfluoroalkylpyrimidine nucleoside analogues have been synthesized, and their biological activity against L1210, S-180, Vero cells, and herpes simplex virus type 1 (HSV-1) was evaluated. The 5-trifluoromethyl derivatives, 7 and 9, showed significant antiviral activity against HSV-1 with ED50 values of 7 and 5 microM, respectively. In addition, the unblocked nucleoside 9 was found to be about 64-fold less toxic to the host Vero cells and gave a favorable therapeutic index of 64 against HSV-1 in vitro.

  DOI：

  10.1021/jm00358a028
• 作为产物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 在 六甲基磷酰三胺 、 碘 、 silver trifluoroacetate 、 铜 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(trifluoromethyl)uracil
  参考文献：
  名称：

  Synthesis and biological activity of 5-(trifluoromethyl)- and 5-(pentafluoroethyl)pyrimidine nucleoside analogs

  摘要：

  Various 5-substituted perfluoroalkylpyrimidine nucleoside analogues have been synthesized, and their biological activity against L1210, S-180, Vero cells, and herpes simplex virus type 1 (HSV-1) was evaluated. The 5-trifluoromethyl derivatives, 7 and 9, showed significant antiviral activity against HSV-1 with ED50 values of 7 and 5 microM, respectively. In addition, the unblocked nucleoside 9 was found to be about 64-fold less toxic to the host Vero cells and gave a favorable therapeutic index of 64 against HSV-1 in vitro.

  DOI：

  10.1021/jm00358a028