(1'S,2'R,3'S)-1'-(6-amino-9H-purin-9-yl)-2',3'-dihydroxycyclopent-4'-ene | 208453-68-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'S,2'R,3'S)-1'-(6-amino-9H-purin-9-yl)-2',3'-dihydroxycyclopent-4'-ene
• 英文别名: (1R,2S,5S)-5-(6-aminopurin-9-yl)cyclopent-3-ene-1,2-diol
• CAS: 208453-68-3
• 化学式: C₁₀H₁₁N₅O₂
• 分子量: 233.23
• InChiKey: RQPALADHFYHEHK-VMHSAVOQSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  556.8±60.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'S,2'R,3'S)-1'-(6-amino-9H-purin-9-yl)-2',3'-dihydroxycyclopent-4'-ene 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 以58%的产率得到(1'S,2'R,3'S)-1'-(6-amino-9H-purin-9-yl)-2',3'-dihydroxycyclopentane
  参考文献：
  名称：

  Does the Anti-Hepatitis B Virus Activity of (+)-5‘-Noraristeromycin Exist in Its 4‘-Epimer and 4‘-Deoxygenated Derivatives?

  摘要：

  To begin an exploration of the structural parameters responsible for the activity of (+)-5'-noraristeromycin toward hepatitis B virus (HBV), three derivatives varied at the C-4' position have been prepared and evaluated. The syntheses began with a Mitsunobu coupling reaction of an appropriate cyclopentanol with B-chloropurine. The products of these reactions were synthetically altered by standard ammonolysis and deprotection procedures to give the desired products. Evaluation of the new derivatives indicated that removal of the C-4' hydroxyl of (+)-5'-noraristeromycin increased its potency toward HBV by approximately 10-fold.

  DOI：

  10.1021/jm980038a
• 作为产物：
  描述：

  (1'S,2'R,3'S)-9-[2',3'-(isopropylidenedioxy)cyclopent-4'-en-1'-yl]-6-chloro-9H-purine 在 Dowex 50X₈ resin 、 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1'S,2'R,3'S)-1'-(6-amino-9H-purin-9-yl)-2',3'-dihydroxycyclopent-4'-ene
  参考文献：
  名称：

  Does the Anti-Hepatitis B Virus Activity of (+)-5‘-Noraristeromycin Exist in Its 4‘-Epimer and 4‘-Deoxygenated Derivatives?

  摘要：

  To begin an exploration of the structural parameters responsible for the activity of (+)-5'-noraristeromycin toward hepatitis B virus (HBV), three derivatives varied at the C-4' position have been prepared and evaluated. The syntheses began with a Mitsunobu coupling reaction of an appropriate cyclopentanol with B-chloropurine. The products of these reactions were synthetically altered by standard ammonolysis and deprotection procedures to give the desired products. Evaluation of the new derivatives indicated that removal of the C-4' hydroxyl of (+)-5'-noraristeromycin increased its potency toward HBV by approximately 10-fold.

  DOI：

  10.1021/jm980038a

文献信息

• Does the Anti-Hepatitis B Virus Activity of (+)-5‘-Noraristeromycin Exist in Its 4‘-Epimer and 4‘-Deoxygenated Derivatives?
  作者：Katherine L. Seley、Stewart W. Schneller、Brent Korba

  DOI：10.1021/jm980038a

  日期：1998.6.1

  To begin an exploration of the structural parameters responsible for the activity of (+)-5'-noraristeromycin toward hepatitis B virus (HBV), three derivatives varied at the C-4' position have been prepared and evaluated. The syntheses began with a Mitsunobu coupling reaction of an appropriate cyclopentanol with B-chloropurine. The products of these reactions were synthetically altered by standard ammonolysis and deprotection procedures to give the desired products. Evaluation of the new derivatives indicated that removal of the C-4' hydroxyl of (+)-5'-noraristeromycin increased its potency toward HBV by approximately 10-fold.