(R)-1-((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)propan-2-yl 2-chloroacetate | 1443988-12-2

• 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: (R)-1-((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)propan-2-yl 2-chloroacetate
• CAS: 1443988-12-2
• 化学式: C₁₈H₂₂Cl₂N₄O₄
• 分子量: 429.303
• InChiKey: ADVHTKLKRLZOCW-YHXLARSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)propan-2-yl 2-chloroacetate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以81%的产率得到(R)-1-((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)propan-2-ol
  参考文献：
  名称：

  6′-Methyl-5′-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5′-homoaristeromycin

  摘要：

  The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.070
• 作为产物：
  描述：

  [(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester 在 偶氮二甲酸二异丙酯 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-1-((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)propan-2-yl 2-chloroacetate
  参考文献：
  名称：

  6′-Methyl-5′-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5′-homoaristeromycin

  摘要：

  The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.070