7-[(3-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]triazolo[4,3-d][1,4]benzothiazin-1-one | 1462405-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 7-[(3-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]triazolo[4,3-d][1,4]benzothiazin-1-one
• 英文别名: 7-[(3-Fluorophenyl)methoxy]-2,4-dihydro-[1,2,4]triazolo[3,4-c][1,4]benzothiazin-1-one；7-[(3-fluorophenyl)methoxy]-2,4-dihydro-[1,2,4]triazolo[3,4-c][1,4]benzothiazin-1-one
• CAS: 1462405-58-8
• 化学式: C₁₆H₁₂FN₃O₂S
• 分子量: 329.355
• InChiKey: QGBARDXLJAQSPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-羟基-4H-苯并[1,4]噻嗪-3-酮 在 劳森试剂 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 、 正丁醇 为溶剂， 反应 0.5h， 生成 7-[(3-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]triazolo[4,3-d][1,4]benzothiazin-1-one
  参考文献：
  名称：

  Synthesis and anticonvulsant activity evaluation of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models

  摘要：

  A novel series of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]-thiazin-1-ones have been synthesized and tested for their anticonvulsant activity using the maximal electroshock (MES) method. The majority of the compounds prepared were effective in the MES screens at a dose level of 100 mg/kg. Of the compounds tested, the most promising was 7-[(4-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]-triazolo[4,3-d][1,4]-benzothiazin-1-one (6m), which showed an ED50 value of 9.2 mg/kg in the MES test in mice. Furthermore, the compound exhibited a PI value of 15.4 which was superior to the standard drug carbamazepine (PI value of 6.4). As well as demonstrating the anti-MES efficacy of compound 6m, its potency against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline were also established, with the results suggesting that several different mechanisms of action might be involved in its anticonvulsant activity, including the inhibition of voltage-gated ion channels and the modulation of GABAergic activity.

  DOI：

  10.1007/s00044-013-0778-y

文献信息

• Synthesis and anticonvulsant activity evaluation of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models
  作者：Xu Cao、Shi-Ben Wang、Xian-Qing Deng、Da-Chuan Liu、Zhe-Shan Quan

  DOI：10.1007/s00044-013-0778-y

  日期：2014.4

  A novel series of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]-thiazin-1-ones have been synthesized and tested for their anticonvulsant activity using the maximal electroshock (MES) method. The majority of the compounds prepared were effective in the MES screens at a dose level of 100 mg/kg. Of the compounds tested, the most promising was 7-[(4-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]-triazolo[4,3-d][1,4]-benzothiazin-1-one (6m), which showed an ED50 value of 9.2 mg/kg in the MES test in mice. Furthermore, the compound exhibited a PI value of 15.4 which was superior to the standard drug carbamazepine (PI value of 6.4). As well as demonstrating the anti-MES efficacy of compound 6m, its potency against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline were also established, with the results suggesting that several different mechanisms of action might be involved in its anticonvulsant activity, including the inhibition of voltage-gated ion channels and the modulation of GABAergic activity.