3-(4-bromobenzyl)piperidine-2,6-dione | 124482-60-6

• 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-(4-bromobenzyl)piperidine-2,6-dione
• 英文别名: 3-[(4-Bromophenyl)methyl]piperidine-2,6-dione
• CAS: 124482-60-6
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: ZPCBMNVJIGYGBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzyl)piperidine-2,6-dione 、 碘甲烷 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 以87%的产率得到3-(4-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
• 作为产物：
  描述：

  戊二酰亚胺 在 potassium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(4-bromobenzyl)piperidine-2,6-dione
  参考文献：
  名称：

  [EN] C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION
  [FR] DÉGRONIMÈRES DE TYPE GLUTARIMIDE LIÉS AU CARBONE C3 POUR LA DÉGRADATION DE PROTÉINES CIBLES

  摘要：

  这项发明提供了一种Degronimers，它具有碳连接的E3泛素连接酶靶向基团（Degrons），可以与一个靶向配体相连，该配体针对的是在体内被选为降解的蛋白质，以及它们的使用方法和组成，以及它们的制备方法。

  公开号：

  WO2017197046A1

文献信息

• C3-carbon linked glutarimide degronimers for target protein degradation
  申请人：C4 Therapeutics, Inc.

  公开号：US10849982B2

  公开（公告）日：2020-12-01

  This invention provides Degronimers that have carbon-linked E3 Ubiquitin Ligase targeting moieties (Degrons), which can be linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

  本发明提供了具有碳连接的 E3 泛素连接酶靶向分子（Degronimers）的 Degronimers（Degronons），这些 Degronimers 可与用于体内降解的蛋白质的靶向配体连接，本发明还提供了其使用方法和组合物及其制备方法。
• 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：——
• C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION
  申请人：C4 Therapeutics, Inc.

  公开号：EP3455218A1

  公开（公告）日：2019-03-20
• [EN] C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION<br/>[FR] DÉGRONIMÈRES DE TYPE GLUTARIMIDE LIÉS AU CARBONE C3 POUR LA DÉGRADATION DE PROTÉINES CIBLES
  申请人：C4 THERAPEUTICS INC

  公开号：WO2017197046A1

  公开（公告）日：2017-11-16

  This invention provides Degronimers that have carbon-linked E3 Ubiquitin Ligase targeting moieties (Degrons), which can be linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

  这项发明提供了一种Degronimers，它具有碳连接的E3泛素连接酶靶向基团（Degrons），可以与一个靶向配体相连，该配体针对的是在体内被选为降解的蛋白质，以及它们的使用方法和组成，以及它们的制备方法。
• 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.