2-amino-6-benzylamino-9-purine | 158982-11-7

• 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: 2-amino-6-benzylamino-9-purine
• 英文别名: N*6*-Benzyl-9-methyl-9H-purine-2,6-diamine；6-N-benzyl-9-methylpurine-2,6-diamine
• CAS: 158982-11-7
• 化学式: C₁₃H₁₄N₆
• 分子量: 254.294
• InChiKey: RQMNYCGUWWTAIT-UHFFFAOYSA-N

物化性质

• 沸点：
  549.3±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-6-benzylamino-9-purine 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.5h， 生成 2-(羟乙氨基)-6-苄氨基-9-甲基嘌呤
  参考文献：
  名称：

  An Efficient Direct Amination of Cyclic Amides and Cyclic Ureas

  摘要：

  [graphics]An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.

  DOI：

  10.1021/ol060815y
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 四丁基氢氧化铵 、 三乙胺 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-amino-6-benzylamino-9-purine
  参考文献：
  名称：

  Cytokinin-Derived Cyclin-Dependent Kinase Inhibitors:  Synthesis and cdc2 Inhibitory Activity of Olomoucine and Related Compounds

  摘要：

  Cyclin-dependent kinases (cdk) have recently raised considerable interest in view of their essential role in the regulation of the cell division cycle. The structure-activity relationships of cdk inhibition showed that the 1, 3, and 7 positions of the purine ring must remain free, probably for a direct interaction, in which it behaves as a hydrogen bond acceptor. Olomoucine (6-(benzylamino)-2-[(2-hydroxyethyl)amino]-9-methylpurine, OC), roscovitine (6-(benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine), and other N-6,2,9-trisubstituted adenines were found to exert a strong inhibitory effect on the p34(cdc2)/cyclin B kinase. Removal or change of the side chain at position 2 or the hydrophobic group at position 9 dramatically decreased the inhibitory activity of olomoucine or roscovitine. Inhibition of cdk with OC and related compounds clearly arrests cell proliferation of many tumor cell lines at G(1)/S and G(2)/M transitions and also triggers apoptosis in the target tumor cells in vitro and in vivo. Thus, from a pharmacological point of view, OC may represent a model compound for a new class of antimitotic and antitumor drugs.

  DOI：

  10.1021/jm960666x

文献信息

• [EN] IMAGING AGENTS FOR NEURAL FLUX<br/>[FR] AGENTS D'IMAGERIE POUR FLUX NEURONAL
  申请人：GEN HOSPITAL CORP

  公开号：WO2016011394A1

  公开（公告）日：2016-01-21

  Provided herein are radiolabeled compounds useful for non-invasive imaging techniques. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography. The present application also provides unlabeled compounds useful in methods of treating diseases of the central nervous system or disease of the peripheral nervous system. Methods for preparing radiolabeled compounds, preparing unlabeled compounds, and diagnostic methods using labeled or unlabeled compounds are also provided.

  本文提供了用于非侵入性成像技术的放射性标记化合物。本文提供的一种示例性放射性标记化合物可用作正电子发射断层扫描的放射示踪剂。本申请还提供了用于治疗中枢神经系统疾病或外周神经系统疾病的未标记化合物。还提供了制备放射性标记化合物、制备未标记化合物以及使用标记化或未标记化化合物的诊断方法。
• The Scope and Mechanism of Phosphonium-Mediated S_NAr Reactions in Heterocyclic Amides and Ureas
  作者：Zhao-Kui Wan、Sumrit Wacharasindhu、Christopher G. Levins、Melissa Lin、Keiko Tabei、Tarek S. Mansour

  DOI：10.1021/jo7020373

  日期：2007.12.1

  An efficient “one-step” synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl

  已经开发了有效的“一步”合成环状am和胍的方法。用六氟磷酸苯并三唑-1-基氧基三（二甲氨基）phosph，碱和氮亲核试剂处理环状酰胺和脲会导致形成相应的环状typically和胍，通常收率高至优异。该方法也已经用于使用苯酚和硫代苯酚亲核试剂制备杂芳基醚和硫醚。时程NMR和HPLC-MS研究促进了所提出的中间体（phospho盐和HOBt加合物）的明确表征。数据揭示了逐步的反应途径。
• Imaging agents for neural flux
  申请人：The General Hospital Corporation

  公开号：US10519160B2

  公开（公告）日：2019-12-31

  Provided herein are radiolabeled compounds useful for non-invasive imaging techniques. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography. The present application also provides unlabeled compounds useful in methods of treating diseases of the central nervous system or disease of the peripheral nervous system. Methods for preparing radiolabeled compounds, preparing unlabeled compounds, and diagnostic methods using labeled or unlabeled compounds are also provided.

  本文提供的放射性标记化合物可用于非侵入性成像技术。本文提供的一种示例性放射性标记化合物可用作正电子发射断层扫描的放射性示踪剂。本申请还提供了用于治疗中枢神经系统疾病或周围神经系统疾病的未标记化合物。还提供了制备放射性标记化合物、制备未标记化合物的方法，以及使用标记或未标记化合物的诊断方法。
• [EN] METHOD TO IDENTIFY REGULATORS OF CDK ACTIVITY<br/>[FR] PROCEDES D'IDENTIFICATION DE REGULATEURS DE L'ACTIVITE DE KINASES DEPENDANTES DES CYCLINES
  申请人：CROPDESIGN NV

  公开号：WO2000033657A1

  公开（公告）日：2000-06-15

  Provided are methods for the identification and isolation of active CDK/cyclin complexes and the constituents thereof and their use for screening of herbicides and plant growth regulators. Furthermore, methods for screening, identifying and obtaining novel plant growth regulators such as activators and inhibitors of plant growth are described. In particular, compounds are provided that are specific for A- and B-type CDKs, respectfully. Such compounds are useful as plant growth regulators and herbicides in agriculture and plant cell and tissue culture.
• Cytokinin-Derived Cyclin-Dependent Kinase Inhibitors:  Synthesis and cdc2 Inhibitory Activity of Olomoucine and Related Compounds
  作者：Libor Havlíček、Jan Hanuš、Jaroslav Veselý、Sophie Leclerc、Laurent Meijer、Gordon Shaw、Miroslav Strnad

  DOI：10.1021/jm960666x

  日期：1997.2.1

  Cyclin-dependent kinases (cdk) have recently raised considerable interest in view of their essential role in the regulation of the cell division cycle. The structure-activity relationships of cdk inhibition showed that the 1, 3, and 7 positions of the purine ring must remain free, probably for a direct interaction, in which it behaves as a hydrogen bond acceptor. Olomoucine (6-(benzylamino)-2-[(2-hydroxyethyl)amino]-9-methylpurine, OC), roscovitine (6-(benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine), and other N-6,2,9-trisubstituted adenines were found to exert a strong inhibitory effect on the p34(cdc2)/cyclin B kinase. Removal or change of the side chain at position 2 or the hydrophobic group at position 9 dramatically decreased the inhibitory activity of olomoucine or roscovitine. Inhibition of cdk with OC and related compounds clearly arrests cell proliferation of many tumor cell lines at G(1)/S and G(2)/M transitions and also triggers apoptosis in the target tumor cells in vitro and in vivo. Thus, from a pharmacological point of view, OC may represent a model compound for a new class of antimitotic and antitumor drugs.