2-吡咯烷酮,3-[(三甲基甲硅烷基)氧代]- | 118581-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2-吡咯烷酮,3-[(三甲基甲硅烷基)氧代]-
• 英文名称: 3-(trimethylsilyloxy)-2-pyrrolidinone
• 英文别名: 3-[(Trimethylsilyl)oxy]pyrrolidin-2-one；3-trimethylsilyloxypyrrolidin-2-one
• CAS: 118581-53-6
• 化学式: C₇H₁₅NO₂Si
• 分子量: 173.287
• InChiKey: KFCHBMSVKKTTFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吡咯烷酮,3-[(三甲基甲硅烷基)氧代]- 、 苯磺酰氯 在 正丁基锂 作用下， 生成 3-hydroxy-1-phenylsulfonyl-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
• 作为产物：
  描述：

  2-羟基-4-氨基丁酸 在 三甲基氯硅烷 、 六甲基二硅氮烷 作用下， 以 邻二甲苯 为溶剂， 生成 2-吡咯烷酮,3-[(三甲基甲硅烷基)氧代]-
  参考文献：
  名称：

  Pyrrolidine 2-one derivatives

  摘要：

  公式为##STR1##的1-取代-2-吡咯酮，其中R.sup.1，R.sup.2和R.sup.3中的一个代表羟基，其余取代基代表氢，能够在动物实验中对抗产生的脑功能不足。它们可用于治疗或预防脑功能不足或提高智力能力。它们可以从新型中间体制造，并可以加工成药物。

  公开号：

  US04461906A1

文献信息

• Pyrrolidinyl benzopyrans as hypotensive agents
  申请人：Beecham Group p.l.c.

  公开号：US04831050A1

  公开（公告）日：1989-05-16

  Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl, or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino, C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl(NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.sub.1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C.sub.1-6 alkyl or by C.sub.2-7 alkanoyl; one of R.sub.3 and R.sub.4 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.3 and R.sub.4 together are C.sub.2-5 polymethylene; either R.sub.5 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 together are a bond; and n is 1 or 2; the hydroxy group substituting the lactam group is other than at position a; and the substituted lactam group being trans to the R.sub.5 group when R.sub.5 is hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy; or a pharmaceutically acceptable salt thereof; having antihypertensive activity, a process for their preparation and their use as pharmaceuticals.

  化合物的公式(I)：##STR1## 其中：R.sub.1和R.sub.2中的任意一个是氢，另一个选自C.sub.1-6烷基羰基，C.sub.1-6烷氧羰基，C.sub.1-6烷基羰氧基，C.sub.1-6烷基羟甲基，硝基，氰基，氯基，三氟甲基，C.sub.1-6烷基磺酰基，C.sub.1-6烷基磺酰基，C.sub.1-6烷氧基磺酰基，C.sub.1-6烷氧基磺酰基，C.sub.1-6烷基羰基氨基，C.sub.1-6烷氧羰基氨基，C.sub.1-6烷基硫代羰基，C.sub.1-6烷氧硫代羰基，C.sub.1-6烷基硫代羰氧基，1-巯基C.sub.2-7烷基，甲酰基或氨基磺酰基，氨基团可选择地被一个或两个C.sub.1-6烷基取代，或C.sub.1-6烷基磺酰基氨基，C.sub.1-6烷基磺酰氨基，C.sub.1-6烷氧基磺酰基氨基或C.sub.1-6烷氧基磺酰氨基，或以C.sub.1-6烷基羰基，硝基或氰基为末端的乙烯基，或--C(C.sub.1-6烷基)(NOH或--C(C.sub.1-6烷基)NNH.sub.2，或R.sub.1和R.sub.2中的一个是硝基，氰基或C.sub.1-3烷基羰基，另一个是甲氧基或氨基，可选择地被一个或两个C.sub.1-6烷基或C.sub.2-7烷酰基取代；R.sub.3和R.sub.4中的一个是氢或C.sub.1-4烷基，另一个是C.sub.1-4烷基或R.sub.3和R.sub.4一起是C.sub.2-5聚亚甲基；R.sub.5是氢，羟基，C.sub.1-6烷氧基或C.sub.1-7酰氧基，R.sub.6是氢或R.sub.5和R.sub.6一起是键；n为1或2；羟基取代内酰胺基团的位置不在a位；当R.sub.5为羟基，C.sub.1-6烷氧基或C.sub.1-7酰氧基时，取代的内酰胺基团与R.sub.5基团相对；或其药学上可接受的盐；具有抗高血压活性，其制备过程以及作为药物的用途。
• ASCHWANDEN, W.;KYBURZ, E.
  作者：ASCHWANDEN, W.、KYBURZ, E.

  DOI：——

  日期：——
• 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.
• Pyrrolidine 2-one derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04461906A1

  公开（公告）日：1984-07-24

  1-Substituted-2-pyrrolidinones of the formula ##STR1## wherein one of R.sup.1, R.sup.2 and R.sup.3 represents hydroxy and the remaining substituents represent hydrogen, are capable of counteracting cerebral insufficiency produced experimentally in animal tests. They can be used therapeutically in the control or prevention of cerebral insufficiency or in the improvement of intellectual capacity. They can be manufactured from novel intermediates and can be processed to provide medicaments.

  公式为##STR1##的1-取代-2-吡咯酮，其中R.sup.1，R.sup.2和R.sup.3中的一个代表羟基，其余取代基代表氢，能够在动物实验中对抗产生的脑功能不足。它们可用于治疗或预防脑功能不足或提高智力能力。它们可以从新型中间体制造，并可以加工成药物。