9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)guanine | 156900-23-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)guanine
• 英文别名: 2-amino-9-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one；2-amino-9-[(2R,3S,5S)-3-fluoro-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 156900-23-1
• 化学式: C₁₀H₁₂FN₅O₃
• 分子量: 269.235
• InChiKey: ZNHBRWZXIMYBEE-DQSPEZDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)guanine 生成 2-amino-6-chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine
  参考文献：
  名称：

  Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

  摘要：

  The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.

  DOI：

  10.1080/15257779408013236
• 作为产物：
  描述：

  2-amino-6-chloro-9-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine 在 sodium hydroxide 作用下， 反应 4.0h， 以47%的产率得到9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)guanine
  参考文献：
  名称：

  Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

  摘要：

  The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.

  DOI：

  10.1080/15257779408013236

文献信息

• 2'-FLUOROFURANOSYL DERIVATIVES AND NOVEL METHOD OF PREPARING 2'-FLUOROPYRIMIDINE AND 2'-FLUOROPURINE NUCLEOSIDES
  申请人：THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce

  公开号：EP0540686B1

  公开（公告）日：1995-08-30
• US5336764A
  申请人：——

  公开号：US5336764A

  公开（公告）日：1994-08-09
• US5495010A
  申请人：——

  公开号：US5495010A

  公开（公告）日：1996-02-27
• US5817799A
  申请人：——

  公开号：US5817799A

  公开（公告）日：1998-10-06
• [EN] 2'-FLUOROFURANOSYL DERIVATIVES AND NOVEL METHOD OF PREPARING 2'-FLUOROPYRIMIDINE AND 2'-FLUOROPURINE NUCLEOSIDES
  申请人：——

  公开号：WO1992001700A1

  公开（公告）日：1992-02-06

  [EN] The instant invention is drawn to 2'-fluoroarabinofuranosyl compounds and a process for preparing same.
  [FR] L'invention concerne des composés de 2'-fluoroarabinofuranosyle et un procédé de préparation de ces composés.