1-(3,4-Methylenedioxyphenyl)-5-oxo-3-pyrrolidinecarboxylic acid | 133748-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(3,4-Methylenedioxyphenyl)-5-oxo-3-pyrrolidinecarboxylic acid
• 英文别名: 1-(1,3-Benzodioxol-5-yl)-5-oxopyrrolidine-3-carboxylic acid
• CAS: 133748-06-8
• 化学式: C₁₂H₁₁NO₅
• mdl: MFCD08444738
• 分子量: 249.223
• InChiKey: GJSWABALJXFXDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-Methylenedioxyphenyl)-5-oxo-3-pyrrolidinecarboxylic acid 在 甲醇 、 sodium tetrahydroborate 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [1-(1,3-Benzodioxol-5-yl)-5-oxopyrrolidin-3-yl]methyl methanesulfonate
  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
• 作为产物：
  描述：

  衣康酸 、 3,4-亚甲二氧基苯胺 以91.3%的产率得到1-(3,4-Methylenedioxyphenyl)-5-oxo-3-pyrrolidinecarboxylic 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

• Pharmacologically active lactam derivatives
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0106988A1

  公开（公告）日：1984-05-02

  Compounds of formula (I) and acid addition salts thereof are of use in medicine in the treatment of prophylaxis of pain, inflammation or fever. The compounds of formula (I) may be prepared by methods analogues to those known in the art. When used in medicine, the compounds of formula (I) may be administered as the compound alone or as a pharmaceutical formulation together with a pharmaceutically acceptable carrier.

  式（I）化合物及其酸加成盐可用于治疗疼痛、炎症或发烧的预防性药物。 式 (I) 化合物可通过与本领域已知方法类似的方法制备。当用于医药时，式 (I) 化合物可作为化合物单独给药，或作为药物制剂与药学上可接受的载体一起给药。
• 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
• Lp(a)-LOWERING AGENTS AND APOPROTEIN (a) PRODUCTION INHIBITORS
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP1000620B1

  公开（公告）日：2005-12-07
• US5145865A
  申请人：——

  公开号：US5145865A

  公开（公告）日：1992-09-08