10-hydrazono-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 10-hydrazono-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide
• 英文别名: 5-hydrazinylidene-6H-benzo[b][1]benzazepine-11-carboxamide
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: WPTQKOQTHLUKHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  奥卡西平 在 盐酸 、 sodium acetate 、 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以46%的产率得到10-hydrazono-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide
  参考文献：
  名称：

  Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives

  摘要：

  A series of novel derivatives of oxcarbazepine (5), 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide was synthesised and evaluated for their anticonvulsant activity and sodium channel blocking properties. The oxime 8 was found to be the most active compound from this series, displaying greater potency than its geometric isomer 9 and exhibiting also the highest protective index value. Importantly, the metabolic profile of 8 differs from the already established dibenz/b,f/azepine-5-carboxamide drugs such as 1 and 5 which undergo rapid and complete conversion in vivo to several biologically active metabolites. In contrast 8 is metabolised to only a very minor extent leading to the conclusion that the observed anti-convulsant effect is solely attributable to 8. It is concluded that 8 may be as effective as 1 and 5 at controlling seizures and that the low toxicity and consequently high protective index should provide the compound with an improved side-effect profile. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01220-x

文献信息

• Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives
  作者：David A Learmonth、Jan Benes、António Parada、Dominik Hainzl、Alexander Beliaev、Maria João Bonifácio、Pedro M Matias、Maria A Carrondo、José Garrett、Patrı́cio Soares-da-Silva

  DOI：10.1016/s0223-5234(01)01220-x

  日期：2001.3

  A series of novel derivatives of oxcarbazepine (5), 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide was synthesised and evaluated for their anticonvulsant activity and sodium channel blocking properties. The oxime 8 was found to be the most active compound from this series, displaying greater potency than its geometric isomer 9 and exhibiting also the highest protective index value. Importantly, the metabolic profile of 8 differs from the already established dibenz/b,f/azepine-5-carboxamide drugs such as 1 and 5 which undergo rapid and complete conversion in vivo to several biologically active metabolites. In contrast 8 is metabolised to only a very minor extent leading to the conclusion that the observed anti-convulsant effect is solely attributable to 8. It is concluded that 8 may be as effective as 1 and 5 at controlling seizures and that the low toxicity and consequently high protective index should provide the compound with an improved side-effect profile. (C) 2001 Editions scientifiques et medicales Elsevier SAS.