7-(pentyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one | 1252018-66-8

• 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-(pentyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one
• 英文别名: 7-pentoxy-4H-1,4-benzothiazin-3-one
• CAS: 1252018-66-8
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: XTJRQNVWPDRTOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(pentyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one 在 劳森试剂 作用下， 以 甲苯 、 正丁醇 为溶剂， 生成 7-(pentyloxy)-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
• 作为产物：
  描述：

  7-甲氧基-1,4-苯并噻嗪-3-酮 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 7-(pentyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-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 of Some 7-Alkoxy-2H-1,4-benzothiazin-3(4H)-ones and 7-Alkoxy-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazines
  作者：Li-Qiu Zhang、Li-Ping Guan、Cheng-Xi Wei、Xian-Qing Deng、Zhe-Shan Quan

  DOI：10.1248/cpb.58.326

  日期：——

  intraperitoneal injection in KunMing mice. Among the synthesized compounds 3a-v, 7-(hexyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one (3f) could be considered potentially the most useful and safe therapeutic compound. Among the synthesized compounds 4a-u, compound 7-(2-fluorobenzyloxy)-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazine (4k) was the most active compound with an ED(50) of 17.0 mg/kg, TD(50) of 243.9 mg/kg

  一系列7-烷氧基-2H-1,4-苯并噻嗪-3（4H）-和一系列新的7-烷氧基-4H- [1,2,4]三唑并[4,3-d]苯并[b]以5-甲氧基苯并[d]噻唑-2-胺为起始原料合成] [1,4]噻嗪衍生物。化合物的结构通过IR，（1）H-NMR光谱数据和显微分析来阐明。在昆明小鼠腹膜内注射后，通过最大电休克（MES）测试和旋转法测试这些化合物的抗惊厥活性。在合成的化合物3a-v中，7-（己氧基）-2H-苯并[b] [1,4]噻嗪-3（4H）-1（3f）可能被认为是最有用和最安全的治疗化合物。在合成的化合物4a-u中，化合物7-（2-氟苄氧基）-4H- [1,2,4]三唑并[4,3-d]苯并[b] [1,4]噻嗪（4k）最多ED（50）为17.0 mg / kg，TD（50）为243的活性化合物。9 mg / kg，保护指数（PI）为14.3。它的神经毒性低于所有其他合成化合物，也显着低于参考药物卡马西平。
• 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.