[(2S,5S)-5-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: [(2S,5S)-5-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid
• 英文别名: [(2S,5S)-5-[(2-amino-6-oxo-1H-purin-9-yl)methyl]tetrahydrofuran-2-yl]phosphonic acid；[(2S,5S)-5-[(2-amino-6-oxo-1H-purin-9-yl)methyl]oxolan-2-yl]phosphonic acid
• 化学式: C₁₀H₁₄N₅O₅P
• 分子量: 315.225
• InChiKey: WMVVWDCCZZNNEX-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 4-二甲氨基吡啶 、 四溴化碳 、 水 、 四氯化钛 、 二异丁基氢化铝 、 caesium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成 [(2S,5S)-5-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid
  参考文献：
  名称：

  Identification of novel nucleotide phosphonate analogs with potent anti-HCMV activity

  摘要：

  We have recently described the discovery of new leads in the area of anti-HCMV research. Further structure - activity relationship studies have allowed us to identify potent and selective anti-HCMV nucleotide analogs. The synthesis as well as structure - activity relationship studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00649-0

文献信息

• Design and SAR Study of a Novel Class of Nucleotide Analogues as Potent Anti-HCMV Agents
  作者：N. Nguyen-ba、L. Chan、M. Quimpère、N. Turcotte、N. Lee、H. Mitchell、J. Bédard

  DOI：10.1080/15257779908041570

  日期：1999.4

  We have developed a novel class of 2-phosphonate 1,3-dioxolane nucleotide analogues, from which the guanine derivative displayed weak anti-HCMV activity. Further SAR studies led to the identification of both cis and trans guanine derivatives of tetrahydrofuran analogues as potent anti-HCMV agents, both in vitro and in vivo, compared to ganciclovir and HPMPC.
• Identification of novel nucleotide phosphonate analogs with potent anti-HCMV activity
  作者：Paul Nguyen-Ba、Nathalie Turcotte、Leonard Yuen、Jean Bédard、Miguel Quimpère、Laval Chan

  DOI：10.1016/s0960-894x(98)00649-0

  日期：1998.12

  We have recently described the discovery of new leads in the area of anti-HCMV research. Further structure - activity relationship studies have allowed us to identify potent and selective anti-HCMV nucleotide analogs. The synthesis as well as structure - activity relationship studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.