4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-2H-pyrrol-2-one | 115653-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-2H-pyrrol-2-one
• 英文别名: 4-(4-fluorophenyl)-1-(4-methoxyphenyl)-1,5-dihydro-2H-pyrrol-2-one；3-(4-fluorophenyl)-1-(4-methoxyphenyl)-2H-pyrrol-5-one
• CAS: 115653-72-0
• 化学式: C₁₇H₁₄FNO₂
• 分子量: 283.302
• InChiKey: DRDDVACKIADGDI-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-2H-pyrrol-2-one 在 盐酸 、 ammonium cerium(IV) nitrate 、 硫酸 、 硝酸 、 lithium diisopropyl amide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 生成 3-ethyl-4-(4-fluoro-3-nitrophenyl)-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
• 作为产物：
  描述：

  4-氟苯乙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 50.17h， 生成 4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-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 A.G.

  公开号：US04737511A1

  公开（公告）日：1988-04-12

  Novel imidazolylphenylpyrrol-2-ones are described as having cardiovascular properties especially as cardiotonic agents in the treatment of congestive heart failure. Pharmaceutical formulations containing such compounds are also described.

  小说咪唑基苯基吡咯-2-酮被描述为具有心血管特性，特别是作为心力衰竭治疗中的强心剂。还描述了含有这些化合物的药物制剂。
• CARDIOTONIC IMIDAZOLYLPHENYLPYRROL-2-ONES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0329691B1

  公开（公告）日：1991-11-21
• ARYL HYDROCARBON RECEPTOR ANTAGONISTS AND METHODS OF USE
  申请人：Magenta Therapeutics Inc.

  公开号：US20210220408A1

  公开（公告）日：2021-07-22

  The disclosure relates to aryl hydrocarbon receptor antagonists as well as methods of modulating aryl hydrocarbon receptor activity and expanding hematopoietic stem cells by culturing hematopoietic stem or progenitor cells in the presence of these agents. Additionally, the disclosure provides methods of treating various pathologies, such as cancer, by administration of these aryl hydrocarbon receptor antagonists. Additionally, the disclosure provides methods of treating various pathologies in a patient by administration of expanded hematopoietic stem cells. The disclosure further provides kits containing aryl hydrocarbon receptor antagonists that can be used for the expansion of hematopoietic stem cells. The disclosure further relates to pharmaceutical compositions comprising the compounds and methods of treating or preventing a disease in which aryl hydrocarbon receptor plays a role.
• US4737511A
  申请人：——

  公开号：US4737511A

  公开（公告）日：1988-04-12