1-(4-羟基苯基)-5-氧代-3-吡咯烷羧酸甲酯 | 133748-30-8

• 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: 1-(4-羟基苯基)-5-氧代-3-吡咯烷羧酸甲酯
• 英文名称: methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate
• 英文别名: (RS)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester；1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester；methyl 1-(4-hydroxyphenyl)-5-oxo-3-pyrrolidinecarboxylate
• CAS: 133748-30-8
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: LNCZWDCYTJRWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-羟基苯基)-5-氧代-3-吡咯烷羧酸甲酯 在 palladium on activated charcoal 甲醇 、 sodium tetrahydroborate 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 methyl 4-<1-(4-hydroxyphenyl)-2-oxo-pyrrolidin-4-yl>-methyloxybenzoate
  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：

  对氨基苯酚 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 1-(4-羟基苯基)-5-氧代-3-吡咯烷羧酸甲酯
  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

• [EN] 1 H-PYRAZOLO[4,3-G]ISOQUINOLINE AND 1 H-PYRAZOLO[4,3-G]QUINOLINE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)<br/>[FR] DÉRIVÉS DE 1H-PYRAZOLO [4,3-G] ISOQUINOLÉINE ET DE 1H-PYRAZOLO [4,3-G] QUINOLÉINE EN TANT QUE MODULATEURS D'ALPHA-1-ANTITRYPSINE POUR TRAITER UNE DÉFICIENCE EN ALPHA-1-ANTITRYPSINE (AATD)
  申请人：VERTEX PHARMA

  公开号：WO2021203025A1

  公开（公告）日：2021-10-07

  1H-pyrazolo[4,3-g]isoquinoline and 1H-pyrazolo[4,3-g]quinoline derivatives as alpha-1-antitrypsin modulators for treating alpha-1- antitrypsin deficiency (AATD).

  1H-吡唑并[4,3-g]异喹啉和1H-吡唑并[4,3-g]喹啉衍生物作为α-1-抗胰蛋白酶调节剂，用于治疗α-1-抗胰蛋白酶缺乏症（AATD）。
• [EN] PYRROLIDONE DERIVATIVES AS MAOB INHIBITORS<br/>[FR] DERIVES DE PYRROLIDONE TELS QUE DES INHIBITEURS MAOB
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004026825A1

  公开（公告）日：2004-04-01

  Racemic or enantiomerically pure 4-pyrrolidino derivatives of the formula (I), processes for their preparation, pharmaceutical compositions comprising said derivatives, and their use in the prevention and treatment of a disease which is mediated by a monoamine oxidase B inhibitor, in particular Alzheimer's disease and senile dementia.

  光学异构体或对映纯的式(I)的4-吡咯啉衍生物，其制备方法，包含该衍生物的药物组合物，以及其在通过单胺氧化酶B抑制剂介导的疾病的预防和治疗中的用途，特别是阿尔茨海默病和老年性痴呆症。
• Process for the preparation of enantiopure pyrrolidin-2-one derivatives
  申请人：Iding Hans

  公开号：US20050065204A1

  公开（公告）日：2005-03-24

  The present invention relates to a process for the preparation of enantiopure intermediates useful in the synthesis of valuable pharmaceutically active compounds, e.g. MAOB inhibitors, and to novel intermediates of formulae I and II wherein R 21 , R 22 , R 23 and R 24 are as defined in the description and claims.

  本发明涉及一种用于制备对合成有价值的药用活性化合物，例如MAOB抑制剂的手性纯中间体的过程，并涉及式I和II的新型中间体，其中R21、R22、R23和R24如描述和权利要求中所定义。
• Phenylcarboxylic acid derivatives having hetero ring
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US05145865A1

  公开（公告）日：1992-09-08

  Phenylcarboxylic acid derivatives having a hetero ring in the substituent of the formula: ##STR1## wherein R.sup.1 is halogen, alkyl, cycloalkyl, hydroxy, alkoxy, phenoxy which has a substituent selected from halogen and alkyl, carboxyl, alkylsulfonyloxy, phenylsulfonyloxy optionally substituted by halogen, alkylsulfonyloxyalkoxy, amino, alkanoylamino, benzoylamino, alkenyloxy, phenylalkoxyalkoxy, hydroxyalkoxy, phenylalkoxy having optionally 1 to 3 substituents selected from halogen, alkyl and alkoxy, halogenoalkyl, cycloalkyloxy optionally substituted by hydroxy, alkoxy substituted by cycloalkyl having optionally hydroxy substituent, imidazolylalkyl or imidazolylalkoxy; k is 0 or 1 to 3; or (R.sup.1).sub.k is alkylenedioxy; A is alkylene or alkylenoxy; l is 0 or 1; B is methylene or carbonyl; m is 0 or 1; D is alkylene; E is alkylene or alkenylene; n is 0 or 1; and R.sup.2 is hydrogen or alkyl, or a salt thereof, which have fatty acid synthesis-inhibitory activity, cholesterol synthesis-inhibitory activity and are useful as antilipidemic agent, prophylactic and treating agent of arteriosclerosis, prophylactic and treating agent of obesity, antidiabetics.

  具有杂环取代基的苯甲酸衍生物的化学式：其中R.sup.1是卤素、烷基、环烷基、羟基、烷氧基、苯氧基，其取代基可选择自卤素和烷基、羧基、烷基磺酰氧基、苯基磺酰氧基，可选择地取代为卤素、烷基磺酰氧基烷氧基、氨基、烷酰胺基、苯甲酰胺基、烯烃氧基、苯基烷氧基烷氧基、羟基烷氧基、苯基烷氧基，其可选择地具有1至3个取代基，选自卤素、烷基和烷氧基、卤代烷基、环烷氧基，可选择地取代为羟基，烷氧基取代为环烷基，其可选择地具有羟基取代基，咪唑基烷基或咪唑基烷氧基；k为0或1至3；或（R.sup.1）.sub.k为亚烷二氧基；A为烷基或烷氧基；l为0或1；B为亚甲基或羰基；m为0或1；D为烷基；E为烷基或烯基；n为0或1；R.sup.2为氢或烷基，或其盐，具有脂肪酸合成抑制活性、胆固醇合成抑制活性并用作抗血脂药物、动脉粥样硬化的预防和治疗药物、肥胖症的预防和治疗药物、抗糖尿病药物。
• Efficient novel eutectic-mixture-mediated synthesis of benzoxazole-linked pyrrolidin-2-one heterocycles
  作者：Yassine Riadi、Oussama Ouerghi、Mohammed H. Geesi、Abdellah Kaiba、El Hassane Anouar、Philippe Guionneau

  DOI：10.1016/j.molliq.2020.115011

  日期：2021.2

  infrared spectroscopy were employed to investigate the structure of the ionic liquid and characterize the DES, respectively. This method exhibited key advantages of high productivity, a short reaction time, and simple processing. Moreover, this DES was easily separated from reaction mixtures and can be recycled for multiple reactions.

  在这项研究中，在新设计的无金属深共熔溶剂（DES）的存在下，采用取代的苄胺和2-氨基苯酚，通过生态高效策略合成了新的苯并恶唑连接的吡咯烷酮杂环化合物。通过使用尿素和合成的甘氨酸衍生的离子液体的低共熔混合物来制备该DES。X射线衍射和红外光谱法分别用于研究离子液体的结构和表征DES。 该方法显示出高生产率，短反应时间和简单加工的主要优点。此外，该DES易于从反应混合物中分离出来，并可循环用于多个反应。