4-(3,4-Dimethoxyphenyl)-2-pyrrolidone | 6891-55-0

• 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-(3,4-Dimethoxyphenyl)-2-pyrrolidone
• 英文别名: 4-(3,4-Dimethoxyphenyl)-2-pyrrolidinon；4-(3,4-Dimethoxyphenyl)-2-pyrrolidon；2-Pyrrolidinone, 4-(3,4-dimethoxyphenyl)-；4-(3,4-dimethoxyphenyl)pyrrolidin-2-one
• CAS: 6891-55-0；132683-33-1；132683-34-2
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: JNRKFSJWVCILHE-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  412.9±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-Dimethoxyphenyl)-2-pyrrolidone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-[3,4-dihydroxyphenyl]-2-pyrrolidone
  参考文献：
  名称：

  4-(Polyalkoxy phenyl)-2-pyrrolidones

  摘要：

  公式为##STR1##的4-(多聚烷氧基苯基)-2-吡咯烷酮，其中R1和R2分别为碳原子数不超过18的碳氢化合物，至少有一个不是甲基，或者是杂环，或者是烷基，其烷基的碳原子数为1-5，被卤素，OH，COOH，烷氧基，烷氧羰基或氨基取代; R'为H，烷基，芳基或酰基; X为O或S; 具有神经精神活性。其中X为O的化合物可通过皂化和脱羧相应的2-吡咯烷酮-3-羧酸烷基酯或环化相应的3-苯基-4-氨基丁酸或其烷基酯来制备。在碱的存在下，可以通过与五硫化二磷反应将吡咯烷酮转化为相应的硫代吡咯烷酮。

  公开号：

  US04193926A1
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氨 、 氢气 、 sodium ethanolate 作用下， 以 四氯化碳 、 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 54.17h， 生成 4-(3,4-Dimethoxyphenyl)-2-pyrrolidone
  参考文献：
  名称：

  (Imidazolylphenyl)pyrrol-2-one inhibitors of cardiac cAMP phosphodiesterase

  摘要：

  Seven 3-alkyl-4-aryl-1,5-dihydro-2H-pyrrol-2-ones were prepared as potential inhibitors of cardiac cAMP phosphodiesterase (PDE). The design of these compounds made use of rolipram, a known inhibitor of the brain cAMP PDE isozyme, as a lead structure and was guided by a model which describes the features required for potent inhibition of the cardiac isozyme. Syntheses for the new compounds are described, together with the results of theoretical and crystallographic studies aimed toward ascertaining their three-dimensional structures. The activities of these compounds as inhibitors of the cardiac and brain cAMP PDE isozymes and their positive inotropic activity in ferret papillary muscle are also reported. Selected compounds were further examined in an in vivo hemodynamic model. One compound,1,5-dihydro-4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-2H-pyrrol-2-one, was identified as a potent and selective positive inotropic agent and inhibitor of cardiac cAMP PDE.

  DOI：

  10.1021/jm00060a012

文献信息

• 4-(Polyalkoxyphenyl)-2-pyrrolidones
  申请人：Schering Aktiengesellschaft

  公开号：US04012495A1

  公开（公告）日：1977-03-15

  4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R.sub.1 and R.sub.2 each are hydrocarbon of up to 18 carbon atoms or alkyl of 1-5 carbon atoms substituted by halogen, OH, COOH, alkoxy, alkoxycarbonyl, carboxamido or amino or collectively are alkylene of 1-3 carbon atoms, R.sub.3 is H or OCH.sub.3, R.sub.4 is H, alkyl, aryl or acyl and X is O or S possess neuropsychotropic activity. The compounds wherein X is O are produced by saponifying and decarboxylating a corresponding 2-pyrrolidone-3-carboxylic acid alkyl ester or cyclizing a corresponding 3-phenyl-4-aminobutyric acid or alkyl ester thereof. The pyrrolidones are converted to corresponding thiopyrrolidones in a conventional manner, e.g., by reaction with phosphorous pentasulfide in the presence of base.

  该文献描述了公式为##STR1##的4-(聚烷氧基苯基)-2-吡咯烷酮，其中R.sub.1和R.sub.2分别是碳原子数高达18个的碳氢化合物或被卤素、羟基、羧基、烷氧基、烷氧羰基、羧酰胺基或氨基取代的1-5个碳原子的烷基，或者是1-3个碳原子的亚烷基，R.sub.3为H或OCH.sub.3，R.sub.4为H、烷基、芳基或酰基，X为O或S，具有神经精神活性。其中X为O的化合物是通过皂化和脱羧化相应的2-吡咯烷酮-3-羧酸烷基酯或者环化相应的3-苯基-4-氨基丁酸或烷基酯制备的。可以采用常规方法将吡咯烷酮转化为相应的硫代吡咯烷酮，例如，在碱的存在下与五硫化二磷反应。
• 4-(Polyalkoxyphenyl)-2-pyrrolidones (II)
  申请人：Schering Aktiengesellschaft

  公开号：US04153713A1

  公开（公告）日：1979-05-08

  4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrocarbon; R.sub.3 is hydrogen or methoxy; R is O-alkyl, O-aryl, O-aralkyl, NH.sub.2, NH-alkyl, NH-aryl, NH-aralkyl, N(alkyl).sub.2, N(aryl).sub.2 or ##STR2## AND X is O or S, are neuropsychotropic agents.

  公式为##STR1##的4-(聚烷氧基苯基)-2-吡咯烷酮，其中R.sub.1和R.sub.2是烃基; R.sub.3是氢或甲氧基; R是O-烷氧基、O-芳基、O-芳基烷基、NH.sub.2、NH-烷基、NH-芳基、NH-芳基烷基、N（烷基）.sub.2、N（芳基）.sub.2或##STR2##并且X是O或S，是神经精神药物。
• Pyrrolidine compound and pharmaceutical use
  申请人：Eisai Co., Ltd.

  公开号：US05444083A1

  公开（公告）日：1995-08-22

  A pyrrolidine compound having the following formula and a pharmacologically acceptable salt thereof is disclosed. It is useful in the pharmaceutical field. ##STR1## in which X is hydrogen, a halogen, or a lower alkyl, Y is --(CH2)n--, n being zero, 1 or 2, --S(O)p--, p being zero, 1 or 2, --O--, or --NH-- and R is phenyl, a substituent-having phenyl, naphtyl, a substituent-having naphthyl, a heteroaryl or a substituent-having heteroaryl.

  本发明公开了一种具有以下公式和其药理学上可接受的盐的吡咯烷化合物。它在制药领域中有用。##STR1## 其中X是氢，卤素或较低的烷基，Y是--（CH2）n--，n为0、1或2，--S（O）p--，p为0、1或2，--O--或--NH--，R是苯基，带有取代基的苯基，萘基，带有取代基的萘基，杂环芳基或带有取代基的杂环芳基。
• PHOSPHODIESTERASE 4 INHIBITORS
  申请人：Ruiping Liu

  公开号：US20090176799A1

  公开（公告）日：2009-07-09

  Selective PDE4 inhibition is achieved by 4-(substituted-phenyl)-2-pyrrolidinone compounds. The compounds exhibit improved PDE4 inhibition as compared to compounds like rolipram and show selectivity with regard to inhibition of other classes of PDEs. The compounds of the present invention are of formula I: wherein R 1 , R 2 , and R 3 are as defined herein.

  选择性PDE4抑制是通过4-(取代苯基)-2-吡咯酮化合物实现的。与类似rolipram的化合物相比，这些化合物表现出更好的PDE4抑制作用，并且在抑制其他类别的PDE方面表现出选择性。本发明的化合物的公式为I：其中R1、R2和R3如本文所定义。
• Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs
  作者：Michel C. Marivet、Jean Jacques Bourguignon、Claire Lugnier、Andre Mann、Jean Claude Stoclet、Camille Georges Wermuth

  DOI：10.1021/jm00127a009

  日期：1989.7

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.