5'-amino-5'-deoxy-2',3'-isopropylidene-inosine | 471923-07-6

• 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: 5'-amino-5'-deoxy-2',3'-isopropylidene-inosine
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1H-purin-6-one
• CAS: 471923-07-6
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: USMBXGRBDUKIGV-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-amino-5'-deoxy-2',3'-isopropylidene-inosine 在 N,N-二异丙基乙胺 作用下， 以 二乙二醇二甲醚 、 正丁醇 为溶剂， 反应 3.5h， 生成 9-((3aR,4R,6R,6aR)-6-((6-(dodecylamino)pyrimidin-4-ylamino)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-purin-6(9H)-one
  参考文献：
  名称：

  Synthesis and antitumor activity of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group

  摘要：

  A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5'-deoxy-5'-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC50 values of 10.73 and 10.99 mu M, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC50 values of 12.71, 8.55 and 8.44, 5.55 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.069
• 作为产物：
  描述：

  N6-苯甲酰基-2',3'-O-异丙亚基腺苷 在 palladium on activated charcoal 吡啶 、 sodium azide 、 phosphate buffer 、 5'-adenylic acid deaminase 、 氢气 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 5'-amino-5'-deoxy-2',3'-isopropylidene-inosine
  参考文献：
  名称：

  Deamination of 5′-substituted-2′,3′-isopropylidene adenosine derivatives catalyzed by adenosine deaminase (ADA, EC 3.5.4.4) and complementary enzymatic biotransformations catalyzed by adenylate deaminase (AMPDA, EC 3.5.4.6): a viable route for the preparation of 5′-substituted inosine derivatives

  摘要：

  Adenosine deaminase (ADA) catalyzes the deamination of 2',3'-isopropylidene adenosine and the corresponding 5'-amino derivative in a 3% dimethylsulfoxide aqueous solution. Whereas ADA is unable to convert other 5'-substituted derivatives (acetate, acetamido, azide), the enzyme adenylate deaminase (AMPDA) accepts all the above compounds as substrates for their biotransformation to the corresponding 5'-substituted inosine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00575-6

文献信息

• Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives
  作者：Silvia Vertuani、Anna Baldisserotto、Katia Varani、Pier Andrea Borea、Bonache De Marcos Maria Cruz、Luca Ferraro、Stefano Manfredini、Alessandro Dalpiaz

  DOI：10.1016/j.ejmech.2012.04.045

  日期：2012.8

  study we present the synthesis and in vitro metabolic stability in human blood and rat liver homogenate of a new class of nucleoside derivatives, in particular 5′-phosphonate adenosine, inosine, guanosine and thioadenosine analogues also modified at the ribose moiety. On the basis of the results obtained we can hypothesize compounds 4 and 18 to have in vivo a relatively high stability.

  核苷衍生物被大量合成和测试以研究其对血小板聚集的影响。众所周知，P2Y受体在调节血小板功能以及控制动脉粥样硬化血栓形成事件中起着重要作用。对抗P2Y 1，特别是P2Y 12受体的化合物的研究对于获得有效预防和治疗动脉血栓形成的血小板聚集抑制剂的目的引起了极大的兴趣。在这项研究中，我们介绍了合成和体外人血和大鼠肝脏匀浆中新一类核苷衍生物的代谢稳定性，特别是在核糖部分也修饰的5'-膦酸酯腺苷，肌苷，鸟苷和硫代腺苷类似物。对结果的基础上获得的，我们可以假设化合物4和18以具有在体内相对高的稳定性。
• Synthesis and antitumor activity of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group
  作者：Kerang Wang、Ling Wu、Zhanbin Qin、Xinhao Yan、Xiaoliu Li、Hua Chen、Pingzhu Zhang、Jinchao Zhang

  DOI：10.1016/j.bmcl.2010.12.069

  日期：2011.2

  A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5'-deoxy-5'-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC50 values of 10.73 and 10.99 mu M, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC50 values of 12.71, 8.55 and 8.44, 5.55 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
• Deamination of 5′-substituted-2′,3′-isopropylidene adenosine derivatives catalyzed by adenosine deaminase (ADA, EC 3.5.4.4) and complementary enzymatic biotransformations catalyzed by adenylate deaminase (AMPDA, EC 3.5.4.6): a viable route for the preparation of 5′-substituted inosine derivatives
  作者：Pierangela Ciuffreda、Angela Loseto、Enzo Santaniello

  DOI：10.1016/s0040-4020(02)00575-6

  日期：2002.7

  Adenosine deaminase (ADA) catalyzes the deamination of 2',3'-isopropylidene adenosine and the corresponding 5'-amino derivative in a 3% dimethylsulfoxide aqueous solution. Whereas ADA is unable to convert other 5'-substituted derivatives (acetate, acetamido, azide), the enzyme adenylate deaminase (AMPDA) accepts all the above compounds as substrates for their biotransformation to the corresponding 5'-substituted inosine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.