3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[4-(4-methyl-pentyl)-phenyl]-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-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[4-(4-methyl-pentyl)-phenyl]-3H-furo[2,3-d]pyrimidin-2-one
• 英文别名: 3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[4-(4-methylpentyl)phenyl]furo[2,3-d]pyrimidin-2-one
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: SPHIFZBIUPXKLW-CEWLAPEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  碘苷 在 ammonium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 silver(I) nitrite 、 碘 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 3-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[4-(4-methyl-pentyl)-phenyl]-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Bicyclic nucleoside inhibitors of Varicella–Zoster virus: The effect of branching in the p-alkylphenyl side chain

  摘要：

  Further to the discovery of bicyclic furanopyrimidine nucleoside analogues (BCNAs) as potent anti-VZV agents, a branched series of this family of compounds was synthesised. The aim was to study the impact of the geometry and steric hindrance in the side chain as well as lipophilic role of this moiety on biological activity. The results showed a detrimental effect of branching on antiviral activity, with a different magnitude depending on the position of branching in the side chain. This study again showed the importance of this moiety for biological activity, as well as the limited efficacy of the ClogP value as a tool for predicting the potency of BCNAs, while suggesting an alternative rationale behind the design of future series. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.071

文献信息

• Bicyclic nucleoside inhibitors of Varicella–Zoster virus: The effect of branching in the p-alkylphenyl side chain
  作者：Giovanna Luoni、Christopher McGuigan、Graciela Andrei、Robert Snoeck、Erik De Clercq、Jan Balzarini

  DOI：10.1016/j.bmcl.2005.05.071

  日期：2005.8

  Further to the discovery of bicyclic furanopyrimidine nucleoside analogues (BCNAs) as potent anti-VZV agents, a branched series of this family of compounds was synthesised. The aim was to study the impact of the geometry and steric hindrance in the side chain as well as lipophilic role of this moiety on biological activity. The results showed a detrimental effect of branching on antiviral activity, with a different magnitude depending on the position of branching in the side chain. This study again showed the importance of this moiety for biological activity, as well as the limited efficacy of the ClogP value as a tool for predicting the potency of BCNAs, while suggesting an alternative rationale behind the design of future series. (c) 2005 Elsevier Ltd. All rights reserved.