1-((3-Acetylphenyl)sulfonyl)-5-ethoxy-2-pyrrolidinone | 111711-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((3-Acetylphenyl)sulfonyl)-5-ethoxy-2-pyrrolidinone
• 英文别名: 1-(3-acetylphenyl)sulfonyl-5-ethoxypyrrolidin-2-one
• CAS: 111711-76-3
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: FBUOKKICTXSLLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-乙氧基-2-吡咯烷酮 、 3-乙酰基苯磺酰氯 在 正丁基锂 作用下， 生成 1-((3-Acetylphenyl)sulfonyl)-5-ethoxy-2-pyrrolidinone
  参考文献：
  名称：

  Amnesia-reversal activity of a series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones

  摘要：

  A series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones were prepared by condensation of arylsulfonyl chlorides with 5-alkoxy-2-pyrrolidinones. Most compounds reversed electroconvulsive shock-induced amnesia in mice, showing the typical inverted U-shaped dose-response curve. The results for 58 compounds indicate that the potency is maximal when there is a 5-ethoxy group and progressively declines as the ether alkyl chain is either elongated or shortened. Substitution on the phenyl ring or its replacement with heterocyclic rings or its hydrogenation decreases the activity. The most promising compounds, with anti-amnesic properties superior in many respects (greater potency, greater efficacy and broader active dose-range) to those of piracetam and aniracetam were further evaluated for reversing scopolamine-induced amnesia and for their anti-hypoxic activity. 5-Ethoxy-1-phenylsulfonyl-2-pyrrolidinone (1) and 5-(1-methylethoxy)-1-/3-(trifluoromethyl) phenylsulfonyl/-2-pyrrolidinone (41) were selected for further evaluation because of their potent anti-amnesic and/or antihypoxic activity.

  DOI：

  10.1016/0223-5234(91)90101-r

文献信息

• Amnesia-reversal activity of a series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones
  作者：E Toja、C Gorini、C Zirotti、F Barzaghi、G Galliani

  DOI：10.1016/0223-5234(91)90101-r

  日期：1991.6

  A series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones were prepared by condensation of arylsulfonyl chlorides with 5-alkoxy-2-pyrrolidinones. Most compounds reversed electroconvulsive shock-induced amnesia in mice, showing the typical inverted U-shaped dose-response curve. The results for 58 compounds indicate that the potency is maximal when there is a 5-ethoxy group and progressively declines as the ether alkyl chain is either elongated or shortened. Substitution on the phenyl ring or its replacement with heterocyclic rings or its hydrogenation decreases the activity. The most promising compounds, with anti-amnesic properties superior in many respects (greater potency, greater efficacy and broader active dose-range) to those of piracetam and aniracetam were further evaluated for reversing scopolamine-induced amnesia and for their anti-hypoxic activity. 5-Ethoxy-1-phenylsulfonyl-2-pyrrolidinone (1) and 5-(1-methylethoxy)-1-/3-(trifluoromethyl) phenylsulfonyl/-2-pyrrolidinone (41) were selected for further evaluation because of their potent anti-amnesic and/or antihypoxic activity.