C-(5-bromo-benzo[d]isoxazol-3-yl)-methanesulfonamide | 68292-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: C-(5-bromo-benzo[d]isoxazol-3-yl)-methanesulfonamide
• 英文别名: 5-Bromo-3-sulfamoylmethyl-1,2-benzisoxazole；(5-Bromo-1,2-benzoxazol-3-yl)methanesulfonamide
• CAS: 68292-17-1
• 化学式: C₈H₇BrN₂O₃S
• 分子量: 291.125
• InChiKey: BCCXQUFATKJCGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5-bromo-benzo[d]isoxazol-3-yl)-methanesulfonyl chloride 在 氨 作用下， 以 乙酸乙酯 为溶剂， 生成 C-(5-bromo-benzo[d]isoxazol-3-yl)-methanesulfonamide
  参考文献：
  名称：

  Studies on 3-substituted 1,2-benzisoxazole derivatives. 6. Syntheses of 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives and their anticonvulsant activities

  摘要：

  Several 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives were synthesized from 3-(bromomethyl)-1,2-benzisoxazole by the reaction with sodium bisulfite followed by chlorination and amination. Some of them displayed marked anticonvulsant activity in mice. The introduction of a halogen atom to the 5 position of the benzisoxazole ring caused increased activity and neurotoxicity; the substitution of a sulfamoyl group caused decreased activity. The activity of monoalkylated compounds might be the result of biotransformation. Among these compounds, 3-(sulfamoylmethyl)-1,2-benzisoxazole (1a) was thought to be the most promising as an anticonvulsant from the ratio of NTD50 and ED50.

  DOI：

  10.1021/jm00188a011

文献信息

• UNO HITOSHI; KUROKAWA MIKIO; MASUDA YOSHINOBU; NISHIMURA HARUKI, J. MED. CHEM., 1979, 22, NO 2, 180-183
  作者：UNO HITOSHI、 KUROKAWA MIKIO、 MASUDA YOSHINOBU、 NISHIMURA HARUKI

  DOI：——

  日期：——
• US4172896A
  申请人：——

  公开号：US4172896A

  公开（公告）日：1979-10-30
• Studies on 3-substituted 1,2-benzisoxazole derivatives. 6. Syntheses of 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives and their anticonvulsant activities
  作者：Hitoshi Uno、Mikio Kurokawa、Yoshinobu Masuda、Haruki Nishimura

  DOI：10.1021/jm00188a011

  日期：1979.2

  Several 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives were synthesized from 3-(bromomethyl)-1,2-benzisoxazole by the reaction with sodium bisulfite followed by chlorination and amination. Some of them displayed marked anticonvulsant activity in mice. The introduction of a halogen atom to the 5 position of the benzisoxazole ring caused increased activity and neurotoxicity; the substitution of a sulfamoyl group caused decreased activity. The activity of monoalkylated compounds might be the result of biotransformation. Among these compounds, 3-(sulfamoylmethyl)-1,2-benzisoxazole (1a) was thought to be the most promising as an anticonvulsant from the ratio of NTD50 and ED50.