(9ci)-5-乙基-2,3-二氢-2-氧代-1H-咪唑-4-羧酸 | 101184-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-5-乙基-2,3-二氢-2-氧代-1H-咪唑-4-羧酸
• 英文名称: 5-ethyl-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylic acid
• 英文别名: 5-ethyl-2-oxoimidazole-4-carboxylic acid；5-ethyl-2-oxo-1,3-dihydroimidazole-4-carboxylic acid
• CAS: 101184-10-5
• 化学式: C₆H₈N₂O₃
• 分子量: 156.141
• InChiKey: BIIBLAGNYXUUEI-UHFFFAOYSA-N

物化性质

• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9ci)-5-乙基-2,3-二氢-2-氧代-1H-咪唑-4-羧酸 、 4-(2-甲基-1H-咪唑-1-基)-苯甲酸 生成 4-ethyl-1,3-dihydro-5-[4-(2-methyl-1H-imidazol-1-yl)benzoyl]-2H-imidazol-2-one
  参考文献：
  名称：

  Cardiotonic 1,3-dihydro-4-[[(imidazol-1-yl)aryl]carbonyl]imidazol-2-ones

  摘要：

  本文描述了一种式为##STR1##的新型咪唑酮酰基芳基咪唑衍生物，具有心血管特性，特别是作为心力衰竭治疗中的强心剂。本文还提供了含有这种化合物的制药配方。此外，本发明还揭示了一种制备这种化合物及其有用中间体的新方法。

  公开号：

  US04556665A1
• 作为产物：
  描述：

  methyl 2-(hydroxyimino)-3-oxopentanoate 在 钯 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 25.0~65.0 ℃ 、344.73 kPa 条件下， 反应 24.0h， 生成 (9ci)-5-乙基-2,3-二氢-2-氧代-1H-咪唑-4-羧酸
  参考文献：
  名称：

  Cardiotonic agents. 5. Fragments from the heterocycle-phenyl-imidazole pharmacophore

  摘要：

  To examine the role of each component in the heterocycle-phenyl-imidazole inotropic pharmacophore, several imidazolone derivatives, an arylimidazole, a substituted 3,4-dihydro-4-oxopyrimidine, and a quinolin-2(1H)-one derivative were prepared as structural fragments or representatives from this relationship. Tests for cardiac inotropic activity in ferret papillary muscle strips (FPM) and for inhibition of crude cAMP phosphodiesterase obtained from canine cardiac tissue suggest that, while all three components contribute significantly toward potent activity (active at less than 1 microM concentrations in FPM), any combination of two components, in approximately a preferred geometry, represents the minimal requirements for weak activity (active at less than 25 microM concentrations). No single component appears to be requisite in an absolute sense.

  DOI：

  10.1021/jm00126a005

文献信息

• Process for the preparation of imidazolonecarbonylarylimidazoles
  申请人：Schering A.G.

  公开号：US04709043A1

  公开（公告）日：1987-11-24

  Novel imidazolonecarbonylarylimidazoles are described having cardiovascular properties, especially as cardiotonic agents in the treatment of congestive heart failure. Pharmaceutical formulations containing such compounds are also provided. Further, a novel process for the preparation of the compounds and intermediates useful thereto of this invention is disclosed.

  本发明描述了具有心血管特性的新型咪唑烷酰基芳基咪唑，特别是作为治疗充血性心力衰竭的心脏强效药物。此外，还提供了含有这种化合物的制药配方。此外，还揭示了一种制备该化合物和中间体的新方法。
• 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.
• Synthesis of 3H-pyrrolo[1,2-c]imidazole-3,5(2H)-diones
  作者：Kenneth J. Shaw、Margaret Vartanian

  DOI：10.1021/jo00002a069

  日期：1991.1
• SHAW, KENNETH J.;VARTANIAN, MARGARET, J. ORG. CHEM., 56,(1991) N, C. 858-861
  作者：SHAW, KENNETH J.、VARTANIAN, MARGARET

  DOI：——

  日期：——
• 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：——