2-(2-hydroxyethylamino)-6-aminopurine | 89897-64-3

• 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-(2-hydroxyethylamino)-6-aminopurine
• 英文别名: 2-(6-amino-7(9)H-purin-2-ylamino)-ethanol；2-<2-Hydroxy-aethylamino>-adenin；2-(6-Amino-9H-purin-2-ylamino)-ethanol；2-[(6-amino-7H-purin-2-yl)amino]ethanol
• CAS: 89897-64-3
• 化学式: C₇H₁₀N₆O
• 分子量: 194.196
• InChiKey: ROBBNTPGIGIHSO-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±52.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  C.I.酸性橙108 、 2-氯-6-氨基嘌呤 反应 3.0h， 以51%的产率得到2-(2-hydroxyethylamino)-6-aminopurine
  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] 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.