5-乙氧基-1-[(4-羟基苯基)磺酰]吡咯烷-2-酮 | 111711-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-乙氧基-1-[(4-羟基苯基)磺酰]吡咯烷-2-酮
• 英文名称: 5-ethoxy-1-(4-hydroxyphenylsulfonyl)-2-pyrrolidinone
• 英文别名: 1-(4-hydroxybenzenesulphonyl)-2-oxo-5-ethoxypyrrolidine；5-Ethoxy-1-((4-hydroxyphenyl)sulfonyl)-2-pyrrolidinone；5-ethoxy-1-(4-hydroxyphenyl)sulfonylpyrrolidin-2-one
• CAS: 111711-93-4
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: WYCLOXANJRCQET-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(苄氧基)苯-1-磺酰氯 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 乙醇 为溶剂， -70.0~25.0 ℃ 、101.33 kPa 条件下， 反应 2.75h， 生成 5-乙氧基-1-[(4-羟基苯基)磺酰]吡咯烷-2-酮
  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

• 1-benzenesulphonyl-2-oxo-5-alkoxypyrrolidines and medical methods of use
  申请人：Roussel Uclaf

  公开号：US04829079A1

  公开（公告）日：1989-05-09

  Memory enhancing 1-(benzenesulfonyl)-2-oxo-5-alkoxy-pyrrolidines are prepared by alkylation of the corresponding pyrrolidones or pyrrolidone precursors.

  记忆增强1-(苯磺酰基)-2-氧代-5-烷氧基-吡咯烷由相应的吡咯烷酮或吡咯烷酮前体的烷基化反应制备。
• Dérivés de la 1-benzène sulfonyl 2-oxo 5-alcoxy pyrrolidine, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0229566B1

  公开（公告）日：1992-05-06
• US4829079A
  申请人：——

  公开号：US4829079A

  公开（公告）日：1989-05-09
• 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.