(3aR,6R,6aS)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxole-4-carboxylic acid | 179929-34-1

• 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: (3aR,6R,6aS)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxole-4-carboxylic acid
• 英文别名: (3aR,6R,6aS)-6-(6-benzamidopurin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole-4-carboxylic acid
• CAS: 179929-34-1
• 化学式: C₂₁H₁₉N₅O₅
• 分子量: 421.412
• InChiKey: XEAMOEMQFRWHDR-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128.46
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aS)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxole-4-carboxylic acid 在 盐酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 反应 75.5h， 生成 (3R,4S,5R)-3-(6-Amino-purin-9-yl)-4,5-dihydroxy-cyclopent-1-enecarboxylic acid methylamide
  参考文献：
  名称：

  New Neplanocin Analogues. V. A Potent Adenosylhomocysteine Hydrolase Inhibitor Lacking Antiviral Activity. Synthesis And Antiviral Activity Of 6″-Carboxylic Acid Derivatives Of Neplanocin A¹

  摘要：

  The g-carboxylic acid derivative of neplanocin A 3 was synthesized from NPA, and was converted to the corresponding methyl ester 4 and amides 5 and 6. These were evaluated for their anti-RNA-virus activities. Of the derivatives synthesized, only 5 was active against RNA viruses within the concentration range of 0.14-4.88 mu g/mL. Compounds 3 and 5 showed a potent inhibitory effect on S-adenosylhomocysteine (AdoHcy) hydrolase from rabbit erythrocytes. Although a close correlation between the inhibitory effect of adenosine analogues on AdoHcy hydrolase and their antiviral potency has been demonstrated, 3 did not show any anti-RNA-virus activities.

  DOI：

  10.1080/07328319608007384
• 作为产物：
  描述：

  N⁶-benzoyl-9-<(1R,2S,3R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 在 sodium chlorite 、 barium permanganate 、 氨基磺酸 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 8.5h， 生成 (3aR,6R,6aS)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxole-4-carboxylic acid
  参考文献：
  名称：

  New Neplanocin Analogues. V. A Potent Adenosylhomocysteine Hydrolase Inhibitor Lacking Antiviral Activity. Synthesis And Antiviral Activity Of 6″-Carboxylic Acid Derivatives Of Neplanocin A¹

  摘要：

  The g-carboxylic acid derivative of neplanocin A 3 was synthesized from NPA, and was converted to the corresponding methyl ester 4 and amides 5 and 6. These were evaluated for their anti-RNA-virus activities. Of the derivatives synthesized, only 5 was active against RNA viruses within the concentration range of 0.14-4.88 mu g/mL. Compounds 3 and 5 showed a potent inhibitory effect on S-adenosylhomocysteine (AdoHcy) hydrolase from rabbit erythrocytes. Although a close correlation between the inhibitory effect of adenosine analogues on AdoHcy hydrolase and their antiviral potency has been demonstrated, 3 did not show any anti-RNA-virus activities.

  DOI：

  10.1080/07328319608007384