3-(2-Bromo-benzyl)-1-methyl-piperidine-2,6-dione | 124482-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(2-Bromo-benzyl)-1-methyl-piperidine-2,6-dione
• 英文别名: 3-[(2-Bromophenyl)methyl]-1-methylpiperidine-2,6-dione
• CAS: 124482-70-8
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: BVDISGUJEGJQSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  戊二酰亚胺 在 氢氧化钾 、 氨 、 sodium 作用下， 以 丙酮 为溶剂， 反应 10.5h， 生成 3-(2-Bromo-benzyl)-1-methyl-piperidine-2,6-dione
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of 2-benzylglutarimides

  摘要：

  A series of 2-benzylglutarimides (4) and their N-methyl analogues (5) were prepared according to the Topliss scheme for the selection of benzyl substituents to maximize anticonvulsant activity. A total of 22 such compounds were subjected to initial (phase I) screening in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazol (scMet) and in the rotorod assay for neurotoxicity. From this series of test compounds, 10 were advanced to quantitative (phase II) testing. Of these, 2-(4-chlorobenzyl)glutarimide (4b) emerged as the most promising anticonvulsant drug candidate by demonstrating both good anti-scMet and anti-MES activity combined with low neurotoxicity after intraperitoneal administration in mice. In drug differentiation tests, 4b was also effective in nontoxic doses against seizures induced by bicuculline, picrotoxin, and strychnine. When compared with the clinically useful drugs phenytoin, carbamazepine, phenobarbital, valproate, and ethosuximide, 4b exhibited an overall pharmacological profile most closely resembling that of valproate.

  DOI：

  10.1021/jm00165a007

文献信息

• GOEHRING, R. RICHARD;GREENWOOD, THOMAS D.;NWOKOGU, GODSON C.;PISIPATI, JU+, J. MED. CHEM., 33,(1990) N, C. 926-931
  作者：GOEHRING, R. RICHARD、GREENWOOD, THOMAS D.、NWOKOGU, GODSON C.、PISIPATI, JU+

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of 2-benzylglutarimides
  作者：R. Richard Goehring、Thomas D. Greenwood、Godson C. Nwokogu、Jyothi S. Pisipati、Tommie G. Rogers、James F. Wolfe

  DOI：10.1021/jm00165a007

  日期：1990.3

  A series of 2-benzylglutarimides (4) and their N-methyl analogues (5) were prepared according to the Topliss scheme for the selection of benzyl substituents to maximize anticonvulsant activity. A total of 22 such compounds were subjected to initial (phase I) screening in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazol (scMet) and in the rotorod assay for neurotoxicity. From this series of test compounds, 10 were advanced to quantitative (phase II) testing. Of these, 2-(4-chlorobenzyl)glutarimide (4b) emerged as the most promising anticonvulsant drug candidate by demonstrating both good anti-scMet and anti-MES activity combined with low neurotoxicity after intraperitoneal administration in mice. In drug differentiation tests, 4b was also effective in nontoxic doses against seizures induced by bicuculline, picrotoxin, and strychnine. When compared with the clinically useful drugs phenytoin, carbamazepine, phenobarbital, valproate, and ethosuximide, 4b exhibited an overall pharmacological profile most closely resembling that of valproate.