methyl 2-(cyanomethyl)-2,3-dimethylbutanoate | 175698-00-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-(cyanomethyl)-2,3-dimethylbutanoate
• 英文别名: methyl 2-cyanomethyl-2,3-dimethylbutanoate
• CAS: 175698-00-7
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: MZRWGRUMWHQNLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(cyanomethyl)-2,3-dimethylbutanoate 在 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以70%的产率得到3-isopropyl-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  3,3-Dialkyl- and 3-Alkyl-3-Benzyl-Substituted 2-Pyrrolidinones:  A New Class of Anticonvulsant Agents

  摘要：

  A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j are the most effective anticonvulsants (ED(50) = 46 and 42 mg/kg, respectively) and have protective index (PI = TD50/ED(50)) values of 5.65 and 3.00, respectively. These protective index values compare favorably to those of the clinically used antiepileptic drugs ethosuximide (ED(50) = 161 mg/kg), phenobarbital (ED(50) = 22 mg/kg), and valproic acid (ED(50) = 133 mg/kg), which have PI values of 2.35, 4.00, and 2.12, respectively. The benzyl compounds [3-substituents are Bn, H (7h); Bn, Me (7i); and Bn, Et (7j)] are also very effective anticonvulsants against seizures induced by maximal electroshock (ED(50) = 41, 55, and 74 mg/kg, respectively) and have PI values of 3.51, 3.04, and 1.70, respectively. The corresponding PI values for phenobarbital and valproic acid are 1.37 and 5.18, respectively. As a class of anticonvulsants, the 3,3-disubstituted 2-pyrrolidinones have a broad spectrum of action and may be useful for the treatment of human epilepsies.

  DOI：

  10.1021/jm9600196
• 作为产物：
  描述：

  butanoic acid, 2,3-dimethyl-, methyl ester 、 溴乙腈 在 lithium diisopropyl amide 作用下， 生成 methyl 2-(cyanomethyl)-2,3-dimethylbutanoate
  参考文献：
  名称：

  3,3-Dialkyl- and 3-Alkyl-3-Benzyl-Substituted 2-Pyrrolidinones:  A New Class of Anticonvulsant Agents

  摘要：

  A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j are the most effective anticonvulsants (ED(50) = 46 and 42 mg/kg, respectively) and have protective index (PI = TD50/ED(50)) values of 5.65 and 3.00, respectively. These protective index values compare favorably to those of the clinically used antiepileptic drugs ethosuximide (ED(50) = 161 mg/kg), phenobarbital (ED(50) = 22 mg/kg), and valproic acid (ED(50) = 133 mg/kg), which have PI values of 2.35, 4.00, and 2.12, respectively. The benzyl compounds [3-substituents are Bn, H (7h); Bn, Me (7i); and Bn, Et (7j)] are also very effective anticonvulsants against seizures induced by maximal electroshock (ED(50) = 41, 55, and 74 mg/kg, respectively) and have PI values of 3.51, 3.04, and 1.70, respectively. The corresponding PI values for phenobarbital and valproic acid are 1.37 and 5.18, respectively. As a class of anticonvulsants, the 3,3-disubstituted 2-pyrrolidinones have a broad spectrum of action and may be useful for the treatment of human epilepsies.

  DOI：

  10.1021/jm9600196

文献信息

• Anticonvulsant and anxiolytic lactam and thiolactam derivatives
  申请人：Washington University

  公开号：US05776959A1

  公开（公告）日：1998-07-07

  This invention relates to lactam and thiolactam derivatives having useful anticonvulsant and anxiolytic activity, pharmaceutical compositions containing these compounds and therapeutic applications using such compositions.

  这项发明涉及具有有用的抗抽搐和抗焦虑活性的内酰胺和硫内酰胺衍生物，含有这些化合物的药物组合物以及使用这些组合物的治疗应用。
• US5776959A
  申请人：——

  公开号：US5776959A

  公开（公告）日：1998-07-07
• US6066666A
  申请人：——

  公开号：US6066666A

  公开（公告）日：2000-05-23
• 3,3-Dialkyl- and 3-Alkyl-3-Benzyl-Substituted 2-Pyrrolidinones:  A New Class of Anticonvulsant Agents
  作者：P. Amruta Reddy、Bonnie C. H. Hsiang、Tammy N. Latifi、Matthew W. Hill、Karen E. Woodward、Steven M. Rothman、James A. Ferrendelli、Douglas F. Covey

  DOI：10.1021/jm9600196

  日期：1996.1.1

  A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j are the most effective anticonvulsants (ED(50) = 46 and 42 mg/kg, respectively) and have protective index (PI = TD50/ED(50)) values of 5.65 and 3.00, respectively. These protective index values compare favorably to those of the clinically used antiepileptic drugs ethosuximide (ED(50) = 161 mg/kg), phenobarbital (ED(50) = 22 mg/kg), and valproic acid (ED(50) = 133 mg/kg), which have PI values of 2.35, 4.00, and 2.12, respectively. The benzyl compounds [3-substituents are Bn, H (7h); Bn, Me (7i); and Bn, Et (7j)] are also very effective anticonvulsants against seizures induced by maximal electroshock (ED(50) = 41, 55, and 74 mg/kg, respectively) and have PI values of 3.51, 3.04, and 1.70, respectively. The corresponding PI values for phenobarbital and valproic acid are 1.37 and 5.18, respectively. As a class of anticonvulsants, the 3,3-disubstituted 2-pyrrolidinones have a broad spectrum of action and may be useful for the treatment of human epilepsies.