1,3-diphenylmethyl-3-methyl-2-piperidinone | 185099-48-3

• 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: 1,3-diphenylmethyl-3-methyl-2-piperidinone
• 英文别名: 3-Methyl-1,3-diphenylmethyl-2-piperidinone；1,3-dibenzyl-3-methylpiperidin-2-one
• CAS: 185099-48-3
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: PCXDSDWOXRBLFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diphenylmethyl-3-methyl-2-piperidinone 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到3-methyl-3-phenylmethyl-2-piperidinone
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activities of 3,3-Dialkyl- and 3-Alkyl-3-benzyl-2-piperidinones (δ-Valerolactams) and Hexahydro-2H-azepin-2-ones (ε-Caprolactams)

  摘要：

  A series of 3-substituted 2-piperidinone (delta-valerolactam) and hexahydro-2H-azepin-2-one (epsilon-caprolactam) derivatives were prepared and evaluated as anticonvulsants in mice. In the 2-piperidinone series, 3,3-diethyl compound 7b is the most effective anticonvulsant against pentylenetetrazole-induced seizures (ED(50), 37 mg/kg; PI (TD50/ED(50)), 4.46), and 3-benzyl compound 4c (ED(50), 41 mg/kg; PI, 7.05) is the most effective anticonvulsant against-seizures induced by maximal electroshock. By contrast, none of the epsilon-caprolactams tested had anticonvulsant effects below doses causing rotorod toxicity. log P values were correlated with neurotoxicity and [S-35]TBPS displacement, but not with anticonvulsant activity. Electrophysiological evaluations of selected compounds from each series indicated that both the delta-valerolactams and epsilon-caprolactams potentiated GABA-mediated chloride currents in rat-hippocampal neurons.

  DOI：

  10.1021/jm960561u
• 作为产物：
  描述：

  3-甲基哌啶-2-酮 在 六甲基磷酰三胺 、 氢氧化钾 、 四丁基硫酸氢铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1,3-diphenylmethyl-3-methyl-2-piperidinone
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activities of 3,3-Dialkyl- and 3-Alkyl-3-benzyl-2-piperidinones (δ-Valerolactams) and Hexahydro-2H-azepin-2-ones (ε-Caprolactams)

  摘要：

  A series of 3-substituted 2-piperidinone (delta-valerolactam) and hexahydro-2H-azepin-2-one (epsilon-caprolactam) derivatives were prepared and evaluated as anticonvulsants in mice. In the 2-piperidinone series, 3,3-diethyl compound 7b is the most effective anticonvulsant against pentylenetetrazole-induced seizures (ED(50), 37 mg/kg; PI (TD50/ED(50)), 4.46), and 3-benzyl compound 4c (ED(50), 41 mg/kg; PI, 7.05) is the most effective anticonvulsant against-seizures induced by maximal electroshock. By contrast, none of the epsilon-caprolactams tested had anticonvulsant effects below doses causing rotorod toxicity. log P values were correlated with neurotoxicity and [S-35]TBPS displacement, but not with anticonvulsant activity. Electrophysiological evaluations of selected compounds from each series indicated that both the delta-valerolactams and epsilon-caprolactams potentiated GABA-mediated chloride currents in rat-hippocampal neurons.

  DOI：

  10.1021/jm960561u

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。
• Lactam and thiolactam derivatives as anesthetic and conscious sedation agents
  申请人：——

  公开号：US20030078283A1

  公开（公告）日：2003-04-24

  This invention relates to lactam and thiolactam derivatives having useful anesthetic and conscious sedation activity. Particularly useful compounds include the diethyl lactams such as 3,3-diethyl-2-pyrrolidinone. Methods for using these compounds and pharmaceutical compositions containing these compounds are provided.

  本发明涉及具有有用的麻醉和意识镇静活性的内酰胺和硫内酰胺衍生物。特别有用的化合物包括二乙基内酰胺，例如3,3-二乙基-2-吡咯酮。提供了使用这些化合物的方法和含有这些化合物的制药组合物。
• 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
• US6680331B2
  申请人：——

  公开号：US6680331B2

  公开（公告）日：2004-01-20