(+/-)-(1'β,2'α,3'α,4'β)-1'-(6-amino-purin-9-yl)-2',3'-(dihydroxy)-4'-(N-hydroxy)amino-cyclopentane

• 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'β,2'α,3'α,4'β)-1'-(6-amino-purin-9-yl)-2',3'-(dihydroxy)-4'-(N-hydroxy)amino-cyclopentane
• 英文别名: (1R,2S,3R,5S)-3-(6-aminopurin-9-yl)-5-(hydroxyamino)cyclopentane-1,2-diol
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: ZKASVFXHAFQVAL-LAHCRNKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-)-(1'β,2'α,3'α,4'β)-1'-(6-amino-purin-9-yl)-2',3'-(dihydroxy)-4'-(N-hydroxy)amino-cyclopentane 在 palladium on activated charcoal 氢气 作用下， 反应 72.0h， 以94%的产率得到5'-amino-5'-deoxy-5'-noraristeromycin
  参考文献：
  名称：

  Synthesis of Novel Carbocyclic Adenosine Analogues as Inhibitors of Adenosine Kinase

  摘要：

  Several new 4'-amino substituted carbocyclic adenosine analogues (6, 7, 31) were prepared as potential inhibitors of the enzyme adenosine kinase. Three different heterocyclic base moieties (adenine, 8-azaadenine, and pyrazolo[3,4-d]pyrimidine) were incorporated into carbocyclic nucleoside analogues through the use of two different synthetic strategies. In both strategies, bicyclic isoxazolidine 9 (prepared through a hetero Diels-Alder reaction with cyclopentadiene) was used as the starting material. In one route, the N-O bond was reductively cleaved, and the hydroxyl group (after inversion and ring functionalization) was used as a leaving group to incorporate the heterocyclic base moiety as the key bond-forming step. A second, more efficient and higher yielding synthetic route was developed as a general solution to the synthesis of the target 4'-amino substituted carbocyclic adenosine analogues. In this methodology, the allylic C-O bond in the bicyclic isoxazolidine 9 was cleaved with double stereoinversion under palladium(0) catalysis as the key bond-forming step to stereospecifically incorporate the heterocyclic base moiety into the cyclopentane ring. The regioselectivity of key bond-forming steps was established principally by NMR methods, especially through (13)C NMR shifts and by NOE effects seen in the analogues, as well as by HMBC/HMQC experiments.

  DOI：

  10.1021/jo981658m
• 作为产物：
  描述：

  5(R)-(6-amino-9H-purin-9-yl)-1(S),2(R)-dihydroxy-3(S)-N-(N-tert-butyloxycarbonylhydroxamino)cyclopentane 在 盐酸 作用下， 反应 4.0h， 以47%的产率得到(+/-)-(1'β,2'α,3'α,4'β)-1'-(6-amino-purin-9-yl)-2',3'-(dihydroxy)-4'-(N-hydroxy)amino-cyclopentane
  参考文献：
  名称：

  Synthesis of Novel Carbocyclic Adenosine Analogues as Inhibitors of Adenosine Kinase

  摘要：

  Several new 4'-amino substituted carbocyclic adenosine analogues (6, 7, 31) were prepared as potential inhibitors of the enzyme adenosine kinase. Three different heterocyclic base moieties (adenine, 8-azaadenine, and pyrazolo[3,4-d]pyrimidine) were incorporated into carbocyclic nucleoside analogues through the use of two different synthetic strategies. In both strategies, bicyclic isoxazolidine 9 (prepared through a hetero Diels-Alder reaction with cyclopentadiene) was used as the starting material. In one route, the N-O bond was reductively cleaved, and the hydroxyl group (after inversion and ring functionalization) was used as a leaving group to incorporate the heterocyclic base moiety as the key bond-forming step. A second, more efficient and higher yielding synthetic route was developed as a general solution to the synthesis of the target 4'-amino substituted carbocyclic adenosine analogues. In this methodology, the allylic C-O bond in the bicyclic isoxazolidine 9 was cleaved with double stereoinversion under palladium(0) catalysis as the key bond-forming step to stereospecifically incorporate the heterocyclic base moiety into the cyclopentane ring. The regioselectivity of key bond-forming steps was established principally by NMR methods, especially through (13)C NMR shifts and by NOE effects seen in the analogues, as well as by HMBC/HMQC experiments.

  DOI：

  10.1021/jo981658m

文献信息

• Synthesis of Novel Carbocyclic Adenosine Analogues as Inhibitors of Adenosine Kinase
  作者：Marlon Cowart、Michael J. Bennett、James F. Kerwin

  DOI：10.1021/jo981658m

  日期：1999.4.1

  Several new 4'-amino substituted carbocyclic adenosine analogues (6, 7, 31) were prepared as potential inhibitors of the enzyme adenosine kinase. Three different heterocyclic base moieties (adenine, 8-azaadenine, and pyrazolo[3,4-d]pyrimidine) were incorporated into carbocyclic nucleoside analogues through the use of two different synthetic strategies. In both strategies, bicyclic isoxazolidine 9 (prepared through a hetero Diels-Alder reaction with cyclopentadiene) was used as the starting material. In one route, the N-O bond was reductively cleaved, and the hydroxyl group (after inversion and ring functionalization) was used as a leaving group to incorporate the heterocyclic base moiety as the key bond-forming step. A second, more efficient and higher yielding synthetic route was developed as a general solution to the synthesis of the target 4'-amino substituted carbocyclic adenosine analogues. In this methodology, the allylic C-O bond in the bicyclic isoxazolidine 9 was cleaved with double stereoinversion under palladium(0) catalysis as the key bond-forming step to stereospecifically incorporate the heterocyclic base moiety into the cyclopentane ring. The regioselectivity of key bond-forming steps was established principally by NMR methods, especially through (13)C NMR shifts and by NOE effects seen in the analogues, as well as by HMBC/HMQC experiments.