4-((E)-{[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid | 650627-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((E)-{[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid
• 英文别名: 4-[(E)-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid
• CAS: 650627-05-7
• 化学式: C₂₀H₁₆N₆O₃
• 分子量: 388.385
• InChiKey: FMUADIGMEFLZAN-AUEPDCJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3-氨基丙基)吡咯烷 、 4-((E)-{[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 3.0h， 以66%的产率得到4-((E)-{[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)-N-(3-pyrrolidin-1-ylpropyl)benzamide
  参考文献：
  名称：

  [EN] PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS
  [FR] INHIBITEURS DE KINASE SOUS FORME DE PYRAZOLOPYRIMIDINES

  摘要：

  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。

  公开号：

  WO2004009602A1
• 作为产物：
  描述：

  3-甲氧基-苯肼 在 四氢吡咯 、 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 61.0h， 生成 4-((E)-{[1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid
  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。
• 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.