7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-{[4-(trifluoromethyl)phenyl]hydrazone} | 914088-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-{[4-(trifluoromethyl)phenyl]hydrazone}
• 英文别名: 9-[[4-(trifluoromethyl)phenyl]hydrazinylidene]-7,8-dihydro-5H-pyrido[3,2-b]azepin-6-one
• CAS: 914088-78-1
• 化学式: C₁₆H₁₃F₃N₄O
• 分子量: 334.301
• InChiKey: SOOGUJWPVCYVTB-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-{[4-(trifluoromethyl)phenyl]hydrazone} 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以50%的产率得到9-trifluoromethyl-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
  参考文献：
  名称：

  9-Cyano-1-azapaullone (Cazpaullone), a Glycogen Synthase Kinase-3 (GSK-3) Inhibitor Activating Pancreatic β Cell Protection and Replication

  摘要：

  Recently, the serine/threonine kinase glycogen synthase kinase-3 (GSK-3) emerged as a regulator of pancreatic beta cell growth and survival. On the basis of the previous observation that GSK-3 inhibitors like 1-azakenpaullone promote beta cell protection and replication, paullone derivatives were synthesized including 1-aza-, 2-aza-, and 12-oxapaullone scaffolds. In enzymatic assays distinct 1-azapaullones were found to exhibit selective GSK-3 inhibitory activity. Within the series of 1-azapaullones, three derivatives stimulated INS-1E beta cell replication and protected INS-1E cells against glucolipotoxicity induced cell death. Cazpaullone (9-cyano-1-azapaullone), the most active compound in the protection assays, also stimulated the replication of primary beta cells in isolated rat islets. Furthermore, cazpaullone showed a pronounced transient stimulation of the mRNA expression of the beta cell transcription factor Pax4, an important regulator of beta cell development and growth. These features distinguish cazpaullone as a unique starting point for the development of beta cell regenerative agents which might be useful in the treatment of diabetes.

  DOI：

  10.1021/jm701582f
• 作为产物：
  描述：

  4-(三氟甲基)苯肼 、 5H-吡啶并[3,2-b]氮杂卓-6,9-(7H,8H)-二酮 在 sodium acetate 、 溶剂黄146 作用下， 以59%的产率得到7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-{[4-(trifluoromethyl)phenyl]hydrazone}
  参考文献：
  名称：

  9-Cyano-1-azapaullone (Cazpaullone), a Glycogen Synthase Kinase-3 (GSK-3) Inhibitor Activating Pancreatic β Cell Protection and Replication

  摘要：

  Recently, the serine/threonine kinase glycogen synthase kinase-3 (GSK-3) emerged as a regulator of pancreatic beta cell growth and survival. On the basis of the previous observation that GSK-3 inhibitors like 1-azakenpaullone promote beta cell protection and replication, paullone derivatives were synthesized including 1-aza-, 2-aza-, and 12-oxapaullone scaffolds. In enzymatic assays distinct 1-azapaullones were found to exhibit selective GSK-3 inhibitory activity. Within the series of 1-azapaullones, three derivatives stimulated INS-1E beta cell replication and protected INS-1E cells against glucolipotoxicity induced cell death. Cazpaullone (9-cyano-1-azapaullone), the most active compound in the protection assays, also stimulated the replication of primary beta cells in isolated rat islets. Furthermore, cazpaullone showed a pronounced transient stimulation of the mRNA expression of the beta cell transcription factor Pax4, an important regulator of beta cell development and growth. These features distinguish cazpaullone as a unique starting point for the development of beta cell regenerative agents which might be useful in the treatment of diabetes.

  DOI：

  10.1021/jm701582f