(2S,3S,4R)-4-(6-chloro-9H-purin-9-yl)-2,3-(isopropylidenedioxy)cyclopent-1-one | 859509-50-5

• 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: (2S,3S,4R)-4-(6-chloro-9H-purin-9-yl)-2,3-(isopropylidenedioxy)cyclopent-1-one
• CAS: 859509-50-5
• 化学式: C₁₃H₁₃ClN₄O₃
• 分子量: 308.724
• InChiKey: GHLNAGVXQUQQTJ-WHFVKQHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  79.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-4-(6-chloro-9H-purin-9-yl)-2,3-(isopropylidenedioxy)cyclopent-1-one 在 二乙胺基三氟化硫 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,3S,5R)-4-(6-amino-9H-purin-9-yl)-3,3-difluoro-1,2-(isopropylidenedioxy)cyclopentane
  参考文献：
  名称：

  The 4′,4′-difluoro analog of 5′-noraristeromycin: A new structural prototype for possible antiviral drug development toward orthopoxvirus and cytomegalovirus

  摘要：

  As a surrogate for 4'-hydroxy-5'-noraristeromycin and related carbocyclic nucleosides, an efficient, enantiodivergent synthetic route to both enantiomers of 5-(6-amino-9H-purin-9-yl)-3,3-difluorocyclopentane-1,2-diol (6 and ent-6) has been developed from a common starting material ((+)-(IR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate, 10). Both compounds were assayed versus a series of viruses. The only response found was for compound 6 toward vaccinia and cowpox (EC50 Of 143 and 94 mu M, respectively) and human cytomegalovirus (EC50 of 6.2 mu M). Both compounds were non-cytotoxic. While not as active as cidofovir toward the orthopox viruses and ganciclovir toward cytomegalovirus, compound 6 offers a new structural prototype upon which to build for uncovering new agents effective against these viral types. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.044
• 作为产物：
  描述：

  9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-6-chloro-9H-purine 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到(2S,3S,4R)-4-(6-chloro-9H-purin-9-yl)-2,3-(isopropylidenedioxy)cyclopent-1-one
  参考文献：
  名称：

  The 4′,4′-difluoro analog of 5′-noraristeromycin: A new structural prototype for possible antiviral drug development toward orthopoxvirus and cytomegalovirus

  摘要：

  As a surrogate for 4'-hydroxy-5'-noraristeromycin and related carbocyclic nucleosides, an efficient, enantiodivergent synthetic route to both enantiomers of 5-(6-amino-9H-purin-9-yl)-3,3-difluorocyclopentane-1,2-diol (6 and ent-6) has been developed from a common starting material ((+)-(IR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate, 10). Both compounds were assayed versus a series of viruses. The only response found was for compound 6 toward vaccinia and cowpox (EC50 Of 143 and 94 mu M, respectively) and human cytomegalovirus (EC50 of 6.2 mu M). Both compounds were non-cytotoxic. While not as active as cidofovir toward the orthopox viruses and ganciclovir toward cytomegalovirus, compound 6 offers a new structural prototype upon which to build for uncovering new agents effective against these viral types. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.044