4-[3-amino-4-(1H-imidazol-1-yl)phenyl]-3-ethyl-1,5-dihydro-2H-pyrrol-2-one | 1027598-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3-amino-4-(1H-imidazol-1-yl)phenyl]-3-ethyl-1,5-dihydro-2H-pyrrol-2-one
• 英文别名: 3-(3-Amino-4-imidazol-1-ylphenyl)-4-ethyl-1,2-dihydropyrrol-5-one
• CAS: 1027598-45-3
• 化学式: C₁₅H₁₆N₄O
• 分子量: 268.318
• InChiKey: XQODKOZFYFOGGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[3-amino-4-(1H-imidazol-1-yl)phenyl]-3-ethyl-1,5-dihydro-2H-pyrrol-2-one 在 盐酸 、 次磷酸 、 copper(II) oxide 、 sodium nitrite 作用下， 反应 1.0h， 生成 3-ethyl-1,5-dihydro-4-[4-(1 H-imidazol-1-yl)phenyl]-2 H-pyrrol-2-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
• 作为产物：
  描述：

  4-氟苯乙酮 在 盐酸 、 ammonium cerium(IV) nitrate 、 硫酸 、 硝酸 、 sodium ethanolate 、 tin(ll) chloride 、 lithium diisopropyl amide 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 60.17h， 生成 4-[3-amino-4-(1H-imidazol-1-yl)phenyl]-3-ethyl-1,5-dihydro-2H-pyrrol-2-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

• 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.