7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-(phenylhydrazone) | 914088-75-8

• 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-(phenylhydrazone)
• 英文别名: 9-(phenylhydrazinylidene)-7,8-dihydro-5H-pyrido[3,2-b]azepin-6-one
• CAS: 914088-75-8
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: XJVQUERPUJWNAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-(phenylhydrazone) 以 二苯醚 为溶剂， 反应 2.0h， 以25%的产率得到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：

  苯肼 、 5H-吡啶并[3,2-b]氮杂卓-6,9-(7H,8H)-二酮 在 溶剂黄146 作用下， 反应 1.0h， 以32%的产率得到7,8-dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-(phenylhydrazone)
  参考文献：
  名称：

  WO2006/117221

  摘要：

  公开号：

文献信息

• Use of Azapaullones For Preventing and Treating Pancreatic Autoimmune Disorders
  申请人：Mussmann Rainer

  公开号：US20080287423A1

  公开（公告）日：2008-11-20

  This invention relates to the use of azapaullones, particularly in combination with immunomodulating agents, in the prevention, and/or treatment of pancreatic autoimmune disorders, e.g. type I diabetes or LADA and neurodegenerative disorders.

  本发明涉及使用阿扎泊隆，特别是与免疫调节剂结合使用，在预防和/或治疗胰腺自身免疫疾病，例如1型糖尿病或LADA和神经退行性疾病方面的应用。
• Use of azapaullones for preventing and treating pancreatic autoimmune disorders
  申请人：Develogen Atkiengesellschaft

  公开号：US07968535B2

  公开（公告）日：2011-06-28

  This invention relates to the use of azapaullones, particularly in combination with immunomodulating agents, in the prevention, and/or treatment of pancreatic autoimmune disorders, e.g. type I diabetes or LADA and neurodegenerative disorders.

  本发明涉及使用阿扎泊隆，特别是与免疫调节剂联合使用，预防和/或治疗胰腺自身免疫疾病，例如I型糖尿病或LADA和神经退行性疾病。