3-(2'-β-fluoro-2'-deoxy-β-D-ribofuranosyl)-6-(4-n-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one | 1201794-39-9

• 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-(2'-β-fluoro-2'-deoxy-β-D-ribofuranosyl)-6-(4-n-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
• 英文别名: 3-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2-one
• CAS: 1201794-39-9
• 化学式: C₂₂H₂₅FN₂O₅
• 分子量: 416.449
• InChiKey: SCFMLLXYJTVSKF-RCLSDMTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-iodo-2'-β-fluoro-2'-deoxyuridine 、 4-戊基苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-(2'-β-fluoro-2'-deoxy-β-D-ribofuranosyl)-6-(4-n-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  2′-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743

  摘要：

  We report the preparation of 2 '-alpha-F, 2 '-beta-F and 2 ',2 '-difluoro analogues of the leading anti-varicella zoster virus (VZV) pentylphenyl BCNA Cf 1743. VZV thymidine kinase showed the highest phosphorylating capacity for the beta-fluoro derivative, that retained equal antiviral potency as the parent compound. In contrast, the alpha-fluoro- and 2 ',2 '-difluoro BCNA derivatives were markedly less (similar to 100-fold) antivirally active. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.116

文献信息

• 2′-Fluorosugar analogues of the highly potent anti-varicella-zoster virus bicyclic nucleoside analogue (BCNA) Cf 1743
  作者：Christopher McGuigan、Marco Derudas、Maurizio Quintiliani、Graciela Andrei、Robert Snoeck、Geoffrey Henson、Jan Balzarini

  DOI：10.1016/j.bmcl.2009.09.116

  日期：2009.11

  We report the preparation of 2 '-alpha-F, 2 '-beta-F and 2 ',2 '-difluoro analogues of the leading anti-varicella zoster virus (VZV) pentylphenyl BCNA Cf 1743. VZV thymidine kinase showed the highest phosphorylating capacity for the beta-fluoro derivative, that retained equal antiviral potency as the parent compound. In contrast, the alpha-fluoro- and 2 ',2 '-difluoro BCNA derivatives were markedly less (similar to 100-fold) antivirally active. (C) 2009 Elsevier Ltd. All rights reserved.