4-<1-(4-t-butylphenyl)-2-oxo-pyrrolidin-4-yl>methyloxybenzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-<1-(4-t-butylphenyl)-2-oxo-pyrrolidin-4-yl>methyloxybenzoic acid
• 英文别名: (+/-)-4-{[1-(tert-butylphenyl)-2-oxo-pyrrolidin-4-yl]methoxy}benzoic acid；4-[1-(4-tert-Butylphenyl)-2-pyrrolidon-4yl]-methoxybenzoic acid；4-[1-(4-tert-butylphenyl)-2-pyrrolidon-4-yl]methoxybenzoic acid；4-[[1-(4-tert-Butylphenyl)-5-oxo-3-pyrrolidinyl]methoxy]benzoic acid；4-[[1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy]benzoic acid
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: YZADMDZNVOBYGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [1-(4-Tert-butylphenyl)-5-oxopyrrolidin-3-yl]methyl methanesulfonate 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-<1-(4-t-butylphenyl)-2-oxo-pyrrolidin-4-yl>methyloxybenzoic acid
  参考文献：
  名称：

  Synthesis of 4-[1-(substituted phenyl)-2-oxo-pyrrolidin-4-yl]methyloxybenzoic acids and related compounds, and their inhibitory capacities toward fatty-acid and sterol biosyntheses

  摘要：

  The synthesis of a series of 4[1-(substituted phenyl)-2-oxo-pyrrolidin-4-yl]methyloxybenzoic acids and related compounds, and their evaluation for inhibitory capacity toward fatty-acid and sterol biosyntheses using rats' liver slices in vitro and rabbits in vivo, are described. Among the compounds synthesized, 7e, 7g, 7h, 7i, 7k, 7r, 21, 23 and 29a b showed a potent inhibitory activity toward fatty-acid and sterol biosyntheses. Their IC(50)s were 4.4-6.8 x 10(-6) M and 6.6-9.8 x 10(-6) M, respectively. These activities were always superior to those of compounds I, II, III and Clinofibrate as references. The inhibitory activity toward the sterol biosynthesis of these compounds was inferior to that of Pravastatin. The reducing effects of the representative compounds (7e and 7l) toward plasma cholesterols and triglyceride were evaluated in Japanese white rabbits (30 and 100 mg/kg, po) and compared with those of Clinofibrate:and Pravastatin; The compounds showed a similar hypocholesterolemic effect to Pravastatin and a more potent hypotriglycemic effect than Clinofibrate and Pravastatin in this animal model. Thus, a dual,action of hypolipidemic effects was noted in 7e and 7l compared with the references.

  DOI：

  10.1016/0223-5234(94)90029-9

文献信息

• OPTICALLY ACTIVE 1-PHENYLPYRROLIDONE DERIVATIVE, INTERMEDIATE FOR PRODUCING THE SAME, AND PROCESS FOR PRODUCING BOTH
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0627419A1

  公开（公告）日：1994-12-07

  An optically active 1-phenylpyrrolidone derivative represented by general formula (I), wherein R represents an optically active α-phenylethylamino group which may be substituted; a 1-phenylpyrrolidone derivative represented by general formula (I-a), and a process for producing 1-phenylpyrrolidone derivatives represented by these formulae.

  由通式(I)代表的光学活性1-苯基吡咯烷酮衍生物，其中R代表可被取代的光学活性α-苯基乙氨基；由通式(I-a)代表的1-苯基吡咯烷酮衍生物，以及生产由这些式子代表的1-苯基吡咯烷酮衍生物的工艺。
• 1-phenylpyrrolidone derivatives having optical activity
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0916657A1

  公开（公告）日：1999-05-19

  An optically active form of a compound represented by the following formula (II) below is useful as an agent for treating hyperlipidemia which has an activity to inhibit the synthesis of fatty acids and an activity to inhibit the synthesis of cholesterol wherein R' is a hydrogen atom or a lower alkyl group such as an alkyl group having 1 to 6 carbon atoms, and a synthesis method for same is described.

  下式(II)代表的化合物的光学活性形式可作为治疗高脂血症的药物，它具有抑制脂肪酸合成的活性和抑制胆固醇合成的活性 其中 R'是氢原子或低级烷基，如具有 1 至 6 个碳原子的烷基，并介绍了其合成方法。
• Lp(a)-LOWERING AGENTS AND APOPROTEIN (a) PRODUCTION INHIBTORS
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP1000620A1

  公开（公告）日：2000-05-17

  Lp(a)-lowering agents or apo(a) production inhibitors containing as the active ingredient phenylcarboxylic acid derivatives represented by general formula (1) or salts thereof, wherein R1 represents optionally substituted phenyl; A represents lower alkylene or lower alkyleneoxy; B represents methylene or carbonyl; D represents lower alkylene; E represents lower alkylene or lower alkenylene; R2 represents hydrogen or lower alkyl; and l, m and n are each 0 or 1. These drugs can significantly lower Lp(a) while scarcely showing any side effects.

  Lp(a)降低剂或apo(a)生成抑制剂，其活性成分为通式(1)代表的苯基羧酸衍生物或其盐类，其中R1代表任选取代的苯基；A代表低级亚烷基或低级亚烷氧基；B代表亚甲基或羰基；D代表低级亚烷基；E代表低级亚烷基或低级亚烯基；R2代表氢或低级亚烷基；l、m和n均为0或1。这些药物可以大大降低脂蛋白（a），同时几乎没有任何副作用。
• Phenylcarboxylic acid derivatives having a hetero ring
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0393607B1

  公开（公告）日：1996-02-21
• OPTICALLY ACTIVE 1-PHENYLPYRROLIDONE DERIVATIVE AND PREPARATION THEREOF
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0627419B1

  公开（公告）日：1999-11-24