2<1-<4-(1H-imidazol-1-yl)phenyl>-2-nitroethyl>-1,3-propanedioic acid diethyl ester | 147471-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2<1-<4-(1H-imidazol-1-yl)phenyl>-2-nitroethyl>-1,3-propanedioic acid diethyl ester
• 英文别名: 1,3-Diethyl 2-[1-[4-(1H-imidazol-1-yl)phenyl]-2-nitroethyl]propanedioate；diethyl 2-[1-(4-imidazol-1-ylphenyl)-2-nitroethyl]propanedioate
• CAS: 147471-15-6
• 化学式: C₁₈H₂₁N₃O₆
• 分子量: 375.381
• InChiKey: ADEQRPODJHYSKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2<1-<4-(1H-imidazol-1-yl)phenyl>-2-nitroethyl>-1,3-propanedioic acid diethyl ester 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 titanium(III) chloride 、 sodium acetate 、 ammonium formate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 calcium chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 17.5h， 生成 4-(4-咪唑-1-基苯基)-3-甲基-1,5-二氢吡咯-2-酮
  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 在 哌啶 、 1,1,2,3-四甲基胍 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 2<1-<4-(1H-imidazol-1-yl)phenyl>-2-nitroethyl>-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