4-肼基-1-(3-甲基苯基)-1H-吡唑并[3,4-d]嘧啶 | 650628-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-肼基-1-(3-甲基苯基)-1H-吡唑并[3,4-d]嘧啶
• 英文名称: 4-hydrazino-1-(3-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 1-(3-Methylphenyl)pyrazolo[5,4-d]pyrimidine-4-ylhydrazine；[1-(3-methylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]hydrazine
• CAS: 650628-07-2
• 化学式: C₁₂H₁₂N₆
• 分子量: 240.267
• InChiKey: DNNRILIYZPCBRP-UHFFFAOYSA-N

物化性质

• 沸点：
  481.2±47.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-吡啶甲醛 、 4-肼基-1-(3-甲基苯基)-1H-吡唑并[3,4-d]嘧啶 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 1-(3-methylphenyl)-N-[(E)-pyridin-4-ylmethylideneamino]pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors

  摘要：

  A series of [1-aryl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]arylhydrazones were discovered as novel inhibitors glycogen synthase kinase-3 (GSK-3). Based on initial modeling a detailed SAR was constructed. Modification of the interior binding aryl ring (Art) determined this to be a tight binding region with little room for modification. As predicted from the model, a large variety of modifications could be incorporated into the hydrazone aryl ring. This work led to GSK-3 inhibitors in the low nano-molar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.036
• 作为产物：
  描述：

  3-甲苯肼 在 水 、 一水合肼 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 56.0h， 生成 4-肼基-1-(3-甲基苯基)-1H-吡唑并[3,4-d]嘧啶
  参考文献：
  名称：

  Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors

  摘要：

  A series of [1-aryl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]arylhydrazones were discovered as novel inhibitors glycogen synthase kinase-3 (GSK-3). Based on initial modeling a detailed SAR was constructed. Modification of the interior binding aryl ring (Art) determined this to be a tight binding region with little room for modification. As predicted from the model, a large variety of modifications could be incorporated into the hydrazone aryl ring. This work led to GSK-3 inhibitors in the low nano-molar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.036

文献信息

• [EN] PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE SOUS FORME DE PYRAZOLOPYRIMIDINES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004009602A1

  公开（公告）日：2004-01-29

  The present invention relates generally to inhibitors of the kinases and more particularly to novel pyrazolopyrimidine compounds.

  本发明一般涉及激酶的抑制剂，更具体地涉及新型吡唑吡嘧啶化合物。
• PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1551841A1

  公开（公告）日：2005-07-13
• Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors
  作者：Andrew J Peat、Joyce A Boucheron、Scott H Dickerson、Dulce Garrido、Wendy Mills、Jennifer Peckham、Frank Preugschat、Terrence Smalley、Stephanie L Schweiker、Jayme R Wilson、Tony Y Wang、Huiqiang Q Zhou、Stephen A Thomson

  DOI：10.1016/j.bmcl.2004.02.036

  日期：2004.5

  A series of [1-aryl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]arylhydrazones were discovered as novel inhibitors glycogen synthase kinase-3 (GSK-3). Based on initial modeling a detailed SAR was constructed. Modification of the interior binding aryl ring (Art) determined this to be a tight binding region with little room for modification. As predicted from the model, a large variety of modifications could be incorporated into the hydrazone aryl ring. This work led to GSK-3 inhibitors in the low nano-molar range. (C) 2004 Elsevier Ltd. All rights reserved.