3-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-pent-4-enyl-3H-furo[2,3-d]pyrimidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-pent-4-enyl-3H-furo[2,3-d]pyrimidin-2-one
• 英文别名: 3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-pent-4-enylfuro[2,3-d]pyrimidin-2-one
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: REUWWECBFMTZLM-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-庚烯-6-炔 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-pent-4-enyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  BICYCLIC NUCLEOSIDE INHIBITORS OF VARICELLA-ZOSTER VIRUS (VZV): EFFECT OF TERMINAL UNSATURATION IN THE SIDE-CHAIN

  摘要：

  As part of an ongoing research program, we have prepared novel bicyclic nucleoside inhibitors bearing long alkyl side-chains for evaluation against VZV. In particular, we report the synthesis of analogues with terminal unsaturation in the side-chain. Terminal alkenyl derivatives were found to be potent antivirals whereas the terminal alkynyls displayed poor activity.

  DOI：

  10.1081/ncn-100002425

文献信息

• Bicyclic nucleoside inhibitors of Varicella-Zoster virus (VZV)
  作者：Sheila Srinivasan、Christopher McGuigan、Graciela Andrei、Robert Snoeck、Erik De Clercq、Jan Balzarini

  DOI：10.1016/s0960-894x(00)00672-7

  日期：2001.2

  Novel bicyclic nucleoside analogues bearing long alkyl side chains are prepared and tested as inhibitors of VZV. In particular, analogues with terminal unsaturation in the side chain are reported. Whilst terminal alkenyl derivatives are potent antivirals, the corresponding terminal alkynyls are poorly active. (C) 2001 Elsevier Science Ltd. All rights reserved.