2-<<4-(1H-imidazol-1-yl)phenyl>methylene>-1,3-propanedioic acid diethyl ester | 147471-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-<<4-(1H-imidazol-1-yl)phenyl>methylene>-1,3-propanedioic acid diethyl ester
• 英文别名: diethyl 2-{[4-(1H-imidazol-1-yl)phenyl]methylene}malonate；diethyl 2-[(4-imidazol-1-ylphenyl)methylidene]propanedioate
• CAS: 147471-14-5
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: COWHYAVISGJLBW-UHFFFAOYSA-N

物化性质

• 沸点：
  440.8±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<<4-(1H-imidazol-1-yl)phenyl>methylene>-1,3-propanedioic acid diethyl ester 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 titanium(III) chloride 、 1,1,2,3-四甲基胍 、 sodium acetate 、 ammonium formate 、 calcium chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 12.5h， 生成 [4-(4-Imidazol-1-ylphenyl)-2-oxopyrrolidin-3-yl]methyl methanesulfonate
  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：

  1-(4-甲醛基苯基)咪唑 、 丙二酸二乙酯 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 28.0h， 以80%的产率得到2-<<4-(1H-imidazol-1-yl)phenyl>methylene>-1,3-propanedioic acid diethyl ester
  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

• (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.