isonicotinaldehyde [1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazone

• 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: isonicotinaldehyde [1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazone
• 英文别名: 1-(1H-benzimidazol-4-yl)-N-[(E)-pyridin-4-ylmethylideneamino]pyrazolo[3,4-d]pyrimidin-4-amine
• 化学式: C₁₈H₁₃N₉
• 分子量: 355.362
• InChiKey: CJOZQFXWSCXETF-KTZMUZOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 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 isonicotinaldehyde [1-(1H-benzimidazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazone
  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

• 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.