methyl-1-oxo-1,2,3,3a-tetrahydropyrrolo<2,1-b>benzothiazol-3a-carboxylate | 155796-04-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl-1-oxo-1,2,3,3a-tetrahydropyrrolo<2,1-b>benzothiazol-3a-carboxylate
• 英文别名: Methyl 1-oxo-2,3-dihydropyrrolo[2,1-b][1,3]benzothiazole-3a-carboxylate；methyl 1-oxo-2,3-dihydropyrrolo[2,1-b][1,3]benzothiazole-3a-carboxylate
• CAS: 155796-04-6
• 化学式: C₁₂H₁₁NO₃S
• 分子量: 249.29
• InChiKey: VXVUKXOASODDMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl-1-oxo-1,2,3,3a-tetrahydropyrrolo<2,1-b>benzothiazol-3a-carboxylate 在 ammonium hydroxide 作用下， 反应 24.0h， 以78%的产率得到1-oxo-1,2,3,3a-tetrahydropyrrolo<2,1-b>benzothiazol-3a-carboxamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of some 1,2,3,3a-tetrahydropyrrolo[2,1-b]benzothiazol-1-ones and pyrrolo[2,1-b]thiazole analogues

  摘要：

  Tetrahydropyrrolo[2,1-b]benzothiazol-1-ones 2a-l and its analogues 3a-d were synthesized and tested as anticonvulsant agents. Some of the compounds were effective against bicuculline-induced seizures in mice. Binding studies with the prepared compounds using [H-3]flunitrazepam as a ligand for the benzodiazepine receptor and [H-3]muscimol for the gamma-aminobutyric acid (GABA) receptor, demonstrate that such compounds have no affinity for these recognition sites. On the contrary, some of these compounds reduced, at very high concentrations, the binding of [S-35]-tert-butylbicyclophosphorothionate ([S-35]TBPS) to recognition sites located at the GABA-coupled chloride channel. However, a lack of correlation between the anticonvulsant activity of these compounds and their capability to displace [S-35]TBPS binding was observed. Furthermore, an in vitro study on the most active compound 2a indicates that this compound may act intact on its target(s) rather than as a hydrolyzed compound 9.

  DOI：

  10.1016/0223-5234(94)90038-8
• 作为产物：
  描述：

  2-氨基苯硫醇 在 硫酸 、 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 methyl-1-oxo-1,2,3,3a-tetrahydropyrrolo<2,1-b>benzothiazol-3a-carboxylate
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of some 1,2,3,3a-tetrahydropyrrolo[2,1-b]benzothiazol-1-ones and pyrrolo[2,1-b]thiazole analogues

  摘要：

  Tetrahydropyrrolo[2,1-b]benzothiazol-1-ones 2a-l and its analogues 3a-d were synthesized and tested as anticonvulsant agents. Some of the compounds were effective against bicuculline-induced seizures in mice. Binding studies with the prepared compounds using [H-3]flunitrazepam as a ligand for the benzodiazepine receptor and [H-3]muscimol for the gamma-aminobutyric acid (GABA) receptor, demonstrate that such compounds have no affinity for these recognition sites. On the contrary, some of these compounds reduced, at very high concentrations, the binding of [S-35]-tert-butylbicyclophosphorothionate ([S-35]TBPS) to recognition sites located at the GABA-coupled chloride channel. However, a lack of correlation between the anticonvulsant activity of these compounds and their capability to displace [S-35]TBPS binding was observed. Furthermore, an in vitro study on the most active compound 2a indicates that this compound may act intact on its target(s) rather than as a hydrolyzed compound 9.

  DOI：

  10.1016/0223-5234(94)90038-8