7-[(4-chlorophenyl)methoxy]-2H-1,4-benzothiazin-3(4H)-one | 1252018-78-2

• 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-[(4-chlorophenyl)methoxy]-2H-1,4-benzothiazin-3(4H)-one
• 英文别名: 7-(4-chloro-benzyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one；7-[(4-chlorophenyl)methoxy]-4H-1,4-benzothiazin-3-one
• CAS: 1252018-78-2
• 化学式: C₁₅H₁₂ClNO₂S
• 分子量: 305.785
• InChiKey: PSHPMADAWGDPPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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-[(4-chlorophenyl)methoxy]-2H-1,4-benzothiazin-3(4H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成
  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 aluminum (III) chloride 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.5h， 生成 7-[(4-chlorophenyl)methoxy]-2H-1,4-benzothiazin-3(4H)-one
  参考文献：
  名称：

  2H-1,4-benzothiazin-3(4H)-ones对单胺氧化酶的抑制作用

  摘要：

  单胺氧化酶 (MAO) 在精神和神经系统疾病（如抑郁症和帕金森病）中起着重要作用。因此，MAO 代表了开发治疗这些疾病的药物的关键目标。本研究旨在合成和发现抑制 MAO 酶的化合物，这些化合物可能与治疗神经系统疾病有关。合成了一系列九个 2 H -1,4-benzothiazin-3(4 H )-ones 并评估其作为人 MAO-A 和 MAO-B 的潜在体外抑制剂。苯并噻嗪酮与一系列 3,4-二氢-2(1 H)-喹啉酮已被证明是高效的 MAO-B 抑制剂。结果表明，苯并噻嗪酮抑制两种 MAO 亚型，但是更有效的 MAO-B 抑制剂。最有效的抑制剂对 MAO-B 的 IC 50值为 0.0027 ( 1b )、0.0082 ( 1c )、0.0096 ( 1d ) 和 0.0041 µM ( 1h )，对 MAO-A 的 IC 50 值为 0.714 µM ( 1d )。这些苯并噻嗪酮衍生物表现出有前途的

  DOI：

  10.1016/j.bmcl.2022.129038

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.
• The inhibition of monoamine oxidase by 2H-1,4-benzothiazin-3(4H)-ones
  作者：Rialette Hitge、Jacobus P. Petzer、Anél Petzer

  DOI：10.1016/j.bmcl.2022.129038

  日期：2022.12

  Monoamine oxidase (MAO) plays an important role in psychiatric and neurological disorders, such as depression and Parkinson's disease. As a result, MAO represents a key target for developing drugs to treat these conditions. The present study aimed to synthesise and discover compounds that inhibit the MAO enzymes and which may be relevant to the treatment of neurological disorders. A series of nine 2H-1,

  单胺氧化酶 (MAO) 在精神和神经系统疾病（如抑郁症和帕金森病）中起着重要作用。因此，MAO 代表了开发治疗这些疾病的药物的关键目标。本研究旨在合成和发现抑制 MAO 酶的化合物，这些化合物可能与治疗神经系统疾病有关。合成了一系列九个 2 H -1,4-benzothiazin-3(4 H )-ones 并评估其作为人 MAO-A 和 MAO-B 的潜在体外抑制剂。苯并噻嗪酮与一系列 3,4-二氢-2(1 H)-喹啉酮已被证明是高效的 MAO-B 抑制剂。结果表明，苯并噻嗪酮抑制两种 MAO 亚型，但是更有效的 MAO-B 抑制剂。最有效的抑制剂对 MAO-B 的 IC 50值为 0.0027 ( 1b )、0.0082 ( 1c )、0.0096 ( 1d ) 和 0.0041 µM ( 1h )，对 MAO-A 的 IC 50 值为 0.714 µM ( 1d )。这些苯并噻嗪酮衍生物表现出有前途的