3-(benzo[d]isoxazol-3-yl)-1-phenylpyrrolidine-2,5-dione | 1621019-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(benzo[d]isoxazol-3-yl)-1-phenylpyrrolidine-2,5-dione
• 英文别名: 3-(1,2-Benzoxazol-3-yl)-1-phenylpyrrolidine-2,5-dione；3-(1,2-benzoxazol-3-yl)-1-phenylpyrrolidine-2,5-dione
• CAS: 1621019-22-4
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: UBSRTJRIDRFKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-羟基苯基)-1-乙酮肟 在 哌啶 、 吡啶 、 盐酸 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 58.0h， 生成 3-(benzo[d]isoxazol-3-yl)-1-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Design and synthesis of new of 3-(benzo[d]isoxazol-3-yl)-1-substituted pyrrolidine-2, 5-dione derivatives as anticonvulsants

  摘要：

  A series of 3-(benzo[d]isoxazol-3-yl)-N-substituted pyrrolidine-2, 5-dione (7a-7d, 8a-8d, 9a-9c) have been prepared and evaluated for their anticonvulsant activities. Preliminary anticonvulsant activity was performed using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests after intraperitoneal (ip) injection into mice, which are the most widely employed models for early identification of anticonvulsant candidate. The acute neurological toxicity (NT) was determined applying rotorod test. The quantitative evaluation after oral administration in rats showed that the most active was 3-(benzo[d]isoxazol-3-yl)-1-(4-fluorophenyl) pyrrolidine-2, 5-dione (8a) with ED50 values of 14.90 mg/kg. Similarly the most potent in scPTZ was 3-(benzo[d]isoxazol-3-yl)-1-cyclohexylpyrrolidine-2, 5-dione (7d) with ED50 values of 42.30 mg/kg. These molecules were more potent and less neurotoxic than phenytoin and ethosuximide which were used as reference antiepileptic drugs.

  DOI：

  10.1016/j.ejmech.2014.07.016