4-((E)-{[1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-((E)-{[1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid
• 英文别名: 4-[(E)-[[1-(1H-benzimidazol-4-yl)pyrazolo[3,4-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid
• 化学式: C₂₀H₁₄N₈O₂
• 分子量: 398.384
• InChiKey: AKYXUYKRNRLTAG-ZNLRHDTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-((E)-{[1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid 、 N,N-二甲基-1,3-二氨基丙烷 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 1.5h， 以12%的产率得到4-((E)-{[1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)-N-[3-(dimethylamino)propyl]benzamide
  参考文献：
  名称：

  [EN] PYRAZOLOPYRIMIDINES AS PROTEIN KINASE INHIBITORS
  [FR] PYRAZOLOPYRIMIDINES EN TANT QU'INHIBITEURS DE KINASES

  摘要：

  公开号：

  WO2004009597A3
• 作为产物：
  描述：

  (3H-benzoimidazol-4-yl)-hydrazine 在 四氢吡咯 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 4-((E)-{[1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazono}methyl)benzoic acid
  参考文献：
  名称：

  Novel GSK-3 inhibitors with improved cellular activity

  摘要：

  A novel series of [1-(1H-benzimidazol-7-yl)-1H-pyrazolo[3,4-d] pyrimidin-4-yl] arylhydrazones was synthesized and shown to potently inhibit glycogen synthase kinase-3 (GSK-3). In light of detailed structure-activity relationships and structural knowledge of the GSK-3 binding pocket, a benzimidazole substituent was incorporated onto the pyrazolopyrimidine ccre resulting in improved potency over previous analogs. More importantly, these derivatives show low nanomolar efficacy for stimulating glycogen synthesis in vitro and therefore may be useful in the treatment of type 2 diabetes mellitus. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.037

文献信息

• Pyrazolopyrimidines as kinase inhibitors
  申请人：Dickerson Howard Scott

  公开号：US20060167020A1

  公开（公告）日：2006-07-27

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

  本发明涉及抑制激酶的化合物，更具体地涉及新型吡唑并嘧啶化合物。
• [EN] PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES EN TANT QU'INHIBITEURS DE KINASES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004009597A2

  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 of formula (I).
• [EN] PYRAZOLOPYRIMIDINES AS PROTEIN KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES EN TANT QU'INHIBITEURS DE KINASES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2004009597A3

  公开（公告）日：2004-05-27
• Novel GSK-3 inhibitors with improved cellular activity
  作者：Andrew J Peat、Dulce Garrido、Joyce A Boucheron、Stephanie L Schweiker、Scott H Dickerson、Jayme R Wilson、Tony Y Wang、Stephen A Thomson

  DOI：10.1016/j.bmcl.2004.02.037

  日期：2004.5

  A novel series of [1-(1H-benzimidazol-7-yl)-1H-pyrazolo[3,4-d] pyrimidin-4-yl] arylhydrazones was synthesized and shown to potently inhibit glycogen synthase kinase-3 (GSK-3). In light of detailed structure-activity relationships and structural knowledge of the GSK-3 binding pocket, a benzimidazole substituent was incorporated onto the pyrazolopyrimidine ccre resulting in improved potency over previous analogs. More importantly, these derivatives show low nanomolar efficacy for stimulating glycogen synthesis in vitro and therefore may be useful in the treatment of type 2 diabetes mellitus. (C) 2004 Elsevier Ltd. All rights reserved.