5-Trifluormethyl-1β-D-arabinofuranosyluracil | 3574-08-1

• 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-Trifluormethyl-1β-D-arabinofuranosyluracil
• 英文别名: 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
• CAS: 3574-08-1
• 化学式: C₁₀H₁₁F₃N₂O₆
• 分子量: 312.202
• InChiKey: UEJHQHNFRZXWRD-MNCSTQPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodouracil 在 盐酸 、 六甲基磷酰三胺 、 铜 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 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