1-[1’,4’-O-anhydro-β-D-psicofuranosyl]uracil | 53263-41-5

• 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: 1-[1’,4’-O-anhydro-β-D-psicofuranosyl]uracil
• 英文别名: 1-(1,4-Anhydro-β-D-psicofuranosyl)uracil；1-(β-D-1,4-anhydro-psicofuranosyl)-1H-pyrimidine-2,4-dione
• CAS: 53263-41-5
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: NVTIBPWYXYQHCG-VPCXQMTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.66
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113.78
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 64.0h， 生成 1-[1’,4’-O-anhydro-β-D-psicofuranosyl]uracil 、 1-(1,3-anhydro-β-D-psicofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and anti-HCV activity of 1-(1′,3′-O-anhydro-3′-C-methyl-β-d-psicofuranosyl)uracil

  摘要：

  Synthesis of a novel 1',2'-oxetane-uridine bearing a 2'-C-methyl substituent, [1-(1',3'-O-anhydro-3'-Cmethyl-beta-D-psicofuranosyl)uracil], is described. Key to its construction was the use of 6-O-(p-toluoy1)1,2:3,4-di-O-isopropylidene-3-C-methyl-D-psicofuranose as a nucleosidation substrate, which itself was derived from D-fructose. Anti-HCV activity was examined for the corresponding triphosphate which was not found to be an inhibitor of HCV NS5B 1b wild type polymerase in vitro. The 1',2'-oxetane uridine triphosphate without 2'-C-methyl substitution was similarly inactive, however, the guanosine analog displayed modest inhibition (IC50= 10 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.069