methyl 1-(4-methoxyphenyl)-2-oxopyrrolidine-4-carboxylate | 133747-97-4

• 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: methyl 1-(4-methoxyphenyl)-2-oxopyrrolidine-4-carboxylate
• 英文别名: methyl 1-(4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylate；methyl 1-(4-methoxyphenyl)-5-oxo-3-pyrrolidinecarboxylate
• CAS: 133747-97-4
• 化学式: C₁₃H₁₅NO₄
• mdl: MFCD00227462
• 分子量: 249.266
• InChiKey: WSZMKQFUWQHLIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methoxyphenyl)-2-oxopyrrolidine-4-carboxylate 在 sodium tetrahydroborate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-(diethoxymethyl)-1-(4-methoxyphenyl)-2-pyrrolidinone
  参考文献：
  名称：

  杂环化合物灭活单胺氧化酶机制的化学模型。电子对缩醛水解的影响

  摘要：

  先前显示单胺氧化酶 (MAO) 会受到 5-(氨基甲基)-3-(4-甲氧基苯基)-2-恶唑烷酮 (3, X=N, Y=O, R=Me, R'= H)、顺-和反-5-(氨基甲基)-3-(4-甲氧基苯基)二氢呋喃-2(3H)-酮(5，R=Me)和4-(氨基甲基)-1-(4-甲氧基苯基) )-2-吡咯烷酮 (6, R=Me)。本文采用两种方法来检验这种抑制的原因是杂环对酶加合物的吸电子稳定性的假设。首先，测量了被抑制酶的再激活率，它们与杂环的吸电子能力的强度定性相关

  DOI：

  10.1021/ja00064a020
• 作为产物：
  描述：

  衣康酸 在 氯化亚砜 作用下， 以 水 为溶剂， 反应 7.5h， 生成 methyl 1-(4-methoxyphenyl)-2-oxopyrrolidine-4-carboxylate
  参考文献：
  名称：

  杂环化合物灭活单胺氧化酶机制的化学模型。电子对缩醛水解的影响

  摘要：

  先前显示单胺氧化酶 (MAO) 会受到 5-(氨基甲基)-3-(4-甲氧基苯基)-2-恶唑烷酮 (3, X=N, Y=O, R=Me, R'= H)、顺-和反-5-(氨基甲基)-3-(4-甲氧基苯基)二氢呋喃-2(3H)-酮(5，R=Me)和4-(氨基甲基)-1-(4-甲氧基苯基) )-2-吡咯烷酮 (6, R=Me)。本文采用两种方法来检验这种抑制的原因是杂环对酶加合物的吸电子稳定性的假设。首先，测量了被抑制酶的再激活率，它们与杂环的吸电子能力的强度定性相关

  DOI：

  10.1021/ja00064a020

文献信息

• 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。
• Transformation of heterocyclic reversible monoamine oxidase-B inactivators into irreversible inactivators by N-methylation
  作者：Charles Z. Ding、Richard B. Silverman

  DOI：10.1021/jm00075a015

  日期：1993.11

  3-[4-[(3-Chlorophenyl)methoxy]phenyl]-5-[(methylamino)methyl]- 2-oxazolidinone (1) is a secondary amine known to be a potent time-dependent irreversible inactivator of monoamine oxidase B (MAO-B). The primary amine analogues of derivatives of 1, as well as of the corresponding dihydrofuranone and pyrrolidinone, had been shown to be time-dependent, but reversible, inhibitors of MAO-B. Here it is shown

  3- [4-[（3-氯苯基）甲氧基]苯基] -5-[（甲基氨基）甲基] -2-恶唑烷酮（1）是一种仲胺，已知是一种有效的时间依赖性不可逆的单胺氧化酶B灭活剂（ MAO-B）。1的衍生物的伯胺类似物，以及相应的二氢呋喃酮和吡咯烷酮，已显示出是时间依赖性的，但可逆的MAO-B抑制剂。此处显示1的伯胺类似物是MAO-B的时间依赖性可逆抑制剂，相应的恶唑烷酮，二氢呋喃酮和吡咯烷酮的仲胺和叔胺类似物是MAO-B的时间依赖性不可逆抑制剂。可以通过升高温度来逆转导致与1形成不可逆酶加合物的反应。
• Thiazolidinedione derivatives or salts thereof and pharmaceutical
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：US05990139A1

  公开（公告）日：1999-11-23

  This invention relates to a thiazolidinedione derivative represented by the following formula (1): ##STR1## wherein R.sup.1 and R.sup.2 individually represent H, a halogen atom, or a halogen-substituted or -unsubstituted lower alkyl or alkoxy group, and R.sup.1 and R.sup.2 may be coupled together to form a ring of an alkylenedioxy chain, X represents a nitrogen atom or a CH group, A represents a substituted or unsubstituted imidazolidinone, pyrrolidinone, imidazole or pyrazole ring, or a salt thereof; and a pharmaceutical composition containing the thiazolidinedione derivative or a salt thereof. The above compound has excellent blood sugar-lowering action and blood lipid-lowering action and is useful as a therapeutic agent for diabetes.

  本发明涉及一种由以下式（1）表示的噻唑烷二酮衍生物：##STR1##其中，R.sup.1和R.sup.2分别表示H，卤素原子或卤素取代或未取代的较低烷基或烷氧基，且R.sup.1和R.sup.2可以耦合形成烷二氧基链的环；X表示氮原子或CH基，A表示取代或未取代的咪唑烷酮，吡咯烷酮，咪唑或吡唑环或其盐；以及含有噻唑烷二酮衍生物或其盐的制药组合物。上述化合物具有出色的降血糖作用和降血脂作用，并可用作糖尿病治疗剂。
• 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。
• 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
  作者：S Watanabe、K Ogawa、T Ohmo、S Yano、H Yamada、T Shirasaka

  DOI：10.1016/0223-5234(94)90029-9

  日期：1994.1

  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.