4-(4-咪唑-1-基苯基)-3-甲基-1,5-二氢吡咯-2-酮 | 115621-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4-咪唑-1-基苯基)-3-甲基-1,5-二氢吡咯-2-酮
• 英文名称: 1,5-dihydro-4-[4-(1 H-imidazol-1-yl)phenyl]-3-methyl-2 H-pyrrol-2-one
• 英文别名: 1,5-dihydro-4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-2H-pyrrol-2-one；1,5-Dihydro-4-(4-(1H-imidazol-1-yl)phenyl)-3-methyl-2H-pyrrol-2-one；3-(4-imidazol-1-ylphenyl)-4-methyl-1,2-dihydropyrrol-5-one
• CAS: 115621-49-3
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: LFSVTQCVEVAXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-甲醛基苯基)咪唑 在 palladium on activated charcoal 哌啶 、 吡啶 、 sodium tetrahydroborate 、 titanium(III) chloride 、 1,1,2,3-四甲基胍 、 sodium acetate 、 ammonium formate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 calcium chloride 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 47.5h， 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

文献信息

• CARDIOTONIC IMIDAZOLYLPHENYLPYRROL-2-ONES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0329691B1

  公开（公告）日：1991-11-21
• US4737511A
  申请人：——

  公开号：US4737511A

  公开（公告）日：1988-04-12
• [EN] CARDIOTONIC IMIDAZOLYLPHENYLPYRROL-2-ONES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1988003531A1

  公开（公告）日：1988-05-19

  (EN) Imidazolylphenylpyrrol-2-ones of one of the formulae (I) and (II), having cardiovascular properties especially as cardiotonic agents in the treatment of congestive heart failure, and pharmaceutical formulations containing such compounds.(FR) Des imidazolylphénylpyrrol-2-ones ayant l'une des formules (I) et (II) présentent des propriétés cardiovasculaires, notamment à titre d'agents cardiotoniques dans le traitement de l'insuffisance cardiaque. Sont également décrites des formulations pharmaceutiques contenant lesdits composés.
• (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.