2-amino-6-chloro-9-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine | 127409-09-0

• 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: 2-amino-6-chloro-9-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine
• 英文别名: [(2S,4S,5R)-5-(2-amino-6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methyl benzoate
• CAS: 127409-09-0
• 化学式: C₁₇H₁₅ClFN₅O₃
• 分子量: 391.789
• InChiKey: WFLXBCPGHWAJBA-ZIBATOQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose 在 氢溴酸 、 氰化汞 、 溶剂黄146 、 牛血清白蛋白 作用下， 反应 9.5h， 生成 2-amino-6-chloro-9-(5-O-benzoyl-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

文献信息

• Purinderivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0349928A2

  公开（公告）日：1990-01-10

  Purinderivate der allgemeinen Formel worin R Chlor, nieder-Alkoxy, nieder-Alkylthio oder Mono(nieder-alkyl)amino ist, haben antivirale Wirksamkeit und können für die Behandlung oder Prophylaxe von humanen oder veterinären viralen Infektionen insbesondere von retroviralen Infektionen wie HIV verwendet werden. Man kann sie aus 2-Amino-9-(5-O-aroyl­-2,3-dideoxy-2-fluor-β-D -threopentofuranosyl)-6-chlor­-9H-purinen herstellen.

  通式如下的嘌呤衍生物 其中 R 为氯、低级烷氧基、低级烷硫基或单（低级烷基）氨基、 具有抗病毒活性，可用于治疗或预防人类或兽类病毒感染，尤其是逆转录病毒感染，如 HIV。它们可由 2-氨基-9-(5-O-芳酰基-2,3-二脱氧-2-氟-β-D-苏氨戊呋喃基)-6-氯-9H-嘌呤制得。
• Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine
  作者：Harry Ford、John S. Driscoll、Maqbool Siddiqui、James A. Kelley、Hioraki Mitsuya、Takuma Shirasaka、David G. Johns、Victor E. Marquez

  DOI：10.1080/15257779408013236

  日期：1994.3

  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.