4-(3’,4’-dimethoxyphenyl)-1H-pyrrol-2(5H)-one | 147471-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3’,4’-dimethoxyphenyl)-1H-pyrrol-2(5H)-one
• 英文别名: 3-(3,4-Dimethoxyphenyl)-1,2-dihydropyrrol-5-one
• CAS: 147471-10-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: UHYNHANXBDSNAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  432.9±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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)-1H-pyrrol-2(5H)-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以65%的产率得到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
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氨 、 sodium ethanolate 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 48.17h， 生成 4-(3’,4’-dimethoxyphenyl)-1H-pyrrol-2(5H)-one
  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

• Synthesis and evaluation of the anti-proliferative activity of diaryl-3-pyrrolin-2-ones and fused analogs
  作者：Patricia Mowery、Fernando Banales Mejia、Courtney L. Franceschi、Maeve H. Kean、Deborah O. Kwansare、Megan M. Lafferty、Namita D. Neerukonda、Carly E. Rolph、Nathanyal J. Truax、Erin T. Pelkey

  DOI：10.1016/j.bmcl.2016.11.076

  日期：2017.1

  Analogs containing a central 3-pyrrolin-2-one core with different methoxyphenyl and/or indole substituents were prepared and tested for anti-proliferative activity in U-937 cells. The most efficacious analogs were non-rigid, (non-fused) contained methoxyaryl groups located at the 4-position, and contained either methoxyaryl or indole groups located at the 3-position. Both the number of methoxy groups

  制备包含具有不同甲氧基苯基和/或吲哚取代基的中心3-吡咯啉-2-酮核的类似物，并测试其在U-937细胞中的抗增殖活性。最有效的类似物是非刚性的（非稠合的），其位于4-位含有甲氧基芳基，并且位于3-位含有甲氧基芳基或吲哚基。取代基中所含的甲氧基的数目以及相对于内酰胺羰基的吲哚环的特定位置均对抗增殖活性具有显着影响。这项工作提供了一个框架，以更好地了解在二芳基杂环支架中诱导抗增殖活性的结构活性关系。
• (Imidazolylphenyl)pyrrol-2-one inhibitors of cardiac cAMP phosphodiesterase
  作者：John W. Lampe、Yuo Ling Chou、Reda G. Hanna、Susan V. Di Meo、Paul W. Erhardt、Alfred A. Hagedorn、William R. Ingebretsen、Elinor Cantor

  DOI：10.1021/jm00060a012

  日期：1993.4

  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.