4-ethyl-1,3-dihydro-5-[4-(1H-imidazol-2-yl)benzoyl]-2H-imidazol-2-one | 94444-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethyl-1,3-dihydro-5-[4-(1H-imidazol-2-yl)benzoyl]-2H-imidazol-2-one
• 英文别名: 4-ethyl-5-[4-(1H-imidazol-2-yl)benzoyl]-1,3-dihydroimidazol-2-one
• CAS: 94444-69-6
• 化学式: C₁₅H₁₄N₄O₂
• 分子量: 282.302
• InChiKey: BNGMNDDKLYSXJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-1,3-dihydro-5-[4-(1H-imidazol-2-yl)benzoyl]-2H-imidazol-2-one 在 sodium methylate 作用下， 以 甲醇 、 丙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-ethyl-6-methyl-7-[4-(1H-imidazol-1-yl)phenyl]pyrrolo[1,2-c]imidazole-3,5(2H,6H)-dione
  参考文献：
  名称：

  Pyrrolo[1,2-c]imidazolone derivatives as PDE inhibitors

  摘要：

  本发明涉及新型吡咯并[1,2-c]咪唑酮及其药学上可接受的盐。本发明中的化合物是PDE抑制剂，主要具有心血管效应，特别是心脏强效作用。

  公开号：

  US04937258A1
• 作为产物：
  描述：

  4-(2-咪唑基)苯甲酸 、 (9ci)-5-乙基-2,3-二氢-2-氧代-1H-咪唑-4-羧酸 在 PPA 作用下， 反应 6.0h， 以6%的产率得到4-ethyl-1,3-dihydro-5-[4-(1H-imidazol-2-yl)benzoyl]-2H-imidazol-2-one
  参考文献：
  名称：

  Cardiotonic agents. 2. (Imidazolyl)aroylimidazolones, highly potent and selective positive inotropic agents

  摘要：

  A series of 4-alkyl-1,3-dihydro-5-[(1H-imidazolyl)benzoyl]-2H-imidazol-2-ones 9 was synthesized and evaluated in vitro for positive inotropic and cyclic AMP phosphodiesterase inhibitory activity. A wide range of inotropic and enzyme-inhibitory potencies was observed, substitution on the imidazolyl moiety being the major determinant of activity. The 4-ethyl-5-[4-(1H-imidazol-1-yl)benzoyl] congener 9g exhibited the highest potency in vitro. Incorporation of a methyl group at the imidazolyl 2-position gave 9h, which was less potent but remarkably selective in vivo for positive inotropic effects over heart rate and hypotensive effects.

  DOI：

  10.1021/jm00391a013

文献信息

• HAGEDORN, A. A., III;ERHARDT, P. W.;LUMMA, W. C., JR.;WOHL, R. A.;CARTOR,+, J. MED. CHEM., 30,(1987) N 8, 1342-1347
  作者：HAGEDORN, A. A., III、ERHARDT, P. W.、LUMMA, W. C., JR.、WOHL, R. A.、CARTOR,+

  DOI：——

  日期：——
• Novel aroylimidazolones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0118790B1

  公开（公告）日：1988-07-06
• US4937258A
  申请人：——

  公开号：US4937258A

  公开（公告）日：1990-06-26
• Cardiotonic agents. 2. (Imidazolyl)aroylimidazolones, highly potent and selective positive inotropic agents
  作者：Alfred A. Hagedorn、Paul W. Erhardt、William C. Lumma、Ronald A. Wohl、Elinor Cantor、Yuo Ling Chou、William R. Ingebretsen、John W. Lampe、David Pang

  DOI：10.1021/jm00391a013

  日期：1987.8

  A series of 4-alkyl-1,3-dihydro-5-[(1H-imidazolyl)benzoyl]-2H-imidazol-2-ones 9 was synthesized and evaluated in vitro for positive inotropic and cyclic AMP phosphodiesterase inhibitory activity. A wide range of inotropic and enzyme-inhibitory potencies was observed, substitution on the imidazolyl moiety being the major determinant of activity. The 4-ethyl-5-[4-(1H-imidazol-1-yl)benzoyl] congener 9g exhibited the highest potency in vitro. Incorporation of a methyl group at the imidazolyl 2-position gave 9h, which was less potent but remarkably selective in vivo for positive inotropic effects over heart rate and hypotensive effects.
• Pyrrolo[1,2-c]imidazolone derivatives as PDE inhibitors
  申请人：Berlex Laboratories, Inc.

  公开号：US04937258A1

  公开（公告）日：1990-06-26

  This invention relates to novel pyrrolo[1,2-c]imidazolones and their pharmaceutically acceptable salts. The compounds of the invention are PDE inhibitors with primarily cardiovascular effects especially cardiotonic effects.

  本发明涉及新型吡咯并[1,2-c]咪唑酮及其药学上可接受的盐。本发明中的化合物是PDE抑制剂，主要具有心血管效应，特别是心脏强效作用。