5-Methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene | 153901-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene
• 英文别名: 5-Methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine
• CAS: 153901-43-0
• 化学式: C₁₇H₁₄N₄S
• 分子量: 306.391
• InChiKey: ZRLZPBMVZCKFPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲胺 、 5-Methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以61%的产率得到Dimethyl-(6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-yl)-amine
  参考文献：
  名称：

  1,5-Benzodiazepines XI. 5-(Dialkylamino) or 5-(alkylthio) substituted 8-chloro-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines with anticonvulsant activity

  摘要：

  The cyclocondensation of (dimethylamino)benzodiazepinones 3a,b with hydrazides yielded triazolobenzodiazepinones 4 which were treated with Lawesson's reagent to give thiolactams 5. The phase-transfer catalyzed (TEBA) alkylation of compounds 5 with suitable alkyl halides afforded 5-(alkylthio)-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines 6a-f. The desired N,N-dialkyl-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines 7a-k were finally obtained from the reaction of the (methylthio)derivatives 6a-d with proper dialkylamines. Compounds 6b-f and 7a-e, g-k were screened for anticonvulsant activity after a preliminary evaluation of their gross behavioral effects and acute toxicity. Nine of the 15 triazolobenzodiazepines tested exerted a clear-cut anticonvulsant effect associated with low acute toxicity. In particular, the most active compounds 6e, f and 7h showed LD50/ED50 ratios that were notably higher than that of phenobarbital and ranging from 50% to 20% of that of diazepam, the latter used as reference drugs.

  DOI：

  10.1016/0223-5234(93)90088-v
• 作为产物：
  描述：

  4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one 在 劳森试剂 、 氢氧化钾 、 苄基三乙基氯化铵 、 溶剂黄146 作用下， 以 氯苯 为溶剂， 反应 2.5h， 生成 5-Methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene
  参考文献：
  名称：

  1,5-Benzodiazepines XI. 5-(Dialkylamino) or 5-(alkylthio) substituted 8-chloro-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines with anticonvulsant activity

  摘要：

  The cyclocondensation of (dimethylamino)benzodiazepinones 3a,b with hydrazides yielded triazolobenzodiazepinones 4 which were treated with Lawesson's reagent to give thiolactams 5. The phase-transfer catalyzed (TEBA) alkylation of compounds 5 with suitable alkyl halides afforded 5-(alkylthio)-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines 6a-f. The desired N,N-dialkyl-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines 7a-k were finally obtained from the reaction of the (methylthio)derivatives 6a-d with proper dialkylamines. Compounds 6b-f and 7a-e, g-k were screened for anticonvulsant activity after a preliminary evaluation of their gross behavioral effects and acute toxicity. Nine of the 15 triazolobenzodiazepines tested exerted a clear-cut anticonvulsant effect associated with low acute toxicity. In particular, the most active compounds 6e, f and 7h showed LD50/ED50 ratios that were notably higher than that of phenobarbital and ranging from 50% to 20% of that of diazepam, the latter used as reference drugs.

  DOI：

  10.1016/0223-5234(93)90088-v