10-(3-chlorobenzyloxy)-5,6-dihydrobenzo[f][1,2,4]triazolo[4,3-d][1,4]oxazepine | 1233880-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 10-(3-chlorobenzyloxy)-5,6-dihydrobenzo[f][1,2,4]triazolo[4,3-d][1,4]oxazepine
• 英文别名: 10-[(3-Chlorophenyl)methoxy]-5,6-dihydro-[1,2,4]triazolo[4,3-d][1,4]benzoxazepine
• CAS: 1233880-86-8
• 化学式: C₁₇H₁₄ClN₃O₂
• 分子量: 327.77
• InChiKey: YMXAICJSFFKSJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-dihydrobenzo[f][1,2,4]triazolo[4,3-d][1,4]oxazepin-10-ol 、 间氯氯苄 在 potassium carbonate 、 苄基三乙基氯化铵 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以61.2%的产率得到10-(3-chlorobenzyloxy)-5,6-dihydrobenzo[f][1,2,4]triazolo[4,3-d][1,4]oxazepine
  参考文献：
  名称：

  Design and synthesis of 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine derivatives with anticonvulsant activity

  摘要：

  A series of novel 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]enzo[f][1,4]oxazepine derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). In the MES test, compound 10-Heptyloxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine (8f) was found to possess better anticonvulsant activity and higher safety than marketed drugs carbamazepine and phenytoin with an ED50 value of 6.9 mg/kg a PI value of 9.5. To explain the possible mechanism of anticonvulsant activity, compound 8f was tested in pentylenetetrazole, isoniazid, thiosemicarbazide, 3-mercaptopropionic acid and Bicuculline induced seizures tests. The results suggest that compound 8f exerts anticonvulsant activity through GABA-mediated mechanism. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.041

文献信息

• Design and synthesis of 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine derivatives with anticonvulsant activity
  作者：Xian-Qing Deng、Cheng-Xi Wei、Fu-Nan Li、Zhi-Gang Sun、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2010.03.041

  日期：2010.7

  A series of novel 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]enzo[f][1,4]oxazepine derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). In the MES test, compound 10-Heptyloxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4]oxazepine (8f) was found to possess better anticonvulsant activity and higher safety than marketed drugs carbamazepine and phenytoin with an ED50 value of 6.9 mg/kg a PI value of 9.5. To explain the possible mechanism of anticonvulsant activity, compound 8f was tested in pentylenetetrazole, isoniazid, thiosemicarbazide, 3-mercaptopropionic acid and Bicuculline induced seizures tests. The results suggest that compound 8f exerts anticonvulsant activity through GABA-mediated mechanism. (c) 2010 Elsevier Masson SAS. All rights reserved.