5-吗啉-4-基-3-苯基-4H-咪唑-2-酮 | 188116-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 5-吗啉-4-基-3-苯基-4H-咪唑-2-酮
• 英文名称: 1-phenyl-4-morpholinoimidazolin-2-one
• 英文别名: 5-morpholin-4-yl-3-phenyl-4H-imidazol-2-one
• CAS: 188116-06-5
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: BOJRVVNXGMREKD-UHFFFAOYSA-N

物化性质

• 熔点：
  246 °C(Solv: ethanol (64-17-5))
• 沸点：
  379.2±52.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基咪唑烷-2,4-二酮 、 吗啡啉盐酸盐 以69%的产率得到5-吗啉-4-基-3-苯基-4H-咪唑-2-酮
  参考文献：
  名称：

  Synthesis, Pharmacology, and Structure−Activity Relationships of Novel Imidazolones and Pyrrolones as Modulators of GABA_A Receptors

  摘要：

  New series of imidazolones and pyrrolones were synthesized. The compounds were tested regarding their anxiolytic properties due to modulation of the GABA(A) receptor response. Several derivatives exhibit considerable pharmacological activity while lacking the typical side effects of benzodiazepine receptor agonists. 1-(4-chlorophenyl)-4-morpholin-1-yl-1,5-dihydro-imidazol-2-one (2) and 1-(4-chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-one (3) were protective in the pentylenetetrazole test in rats with oral ED50 of 27.4 and 12.8 mg/kg and TD50 (rotarod) of > 500 and 265 mg/kg, respectively. The minimum effective dose in the Vogel conflict test was 3 mg/kg for both compounds. Common structure-activity relationship and comparative molecular field analysis models of the various series of derivatives could be established which are in accordance with a GABAA mediated pharmacological action. The findings fit well into an established pharmacophore model. This model is refined by an additional steric restriction feature.

  DOI：

  10.1021/jm0509400

文献信息

• [DE] NEUE, ANTIKONVULSIV WIRKENDE 1-AR(ALK)YL-IMIDAZOLIN-2-ONE, DIE IN 4-STELLUNG EINEN DISUBSTITUIERTEN AMIN-REST ENTHALTEN, UND VERFAHREN ZU DEREN HERSTELLUNG<br/>[EN] NOVEL 1-AR(ALK)YL-IMIDAZOLIN-2-ONES CONTAINING A DISUBSTITUTED AMINE RADICAL IN THE 4TH POSITION, HAVING AN ANTI-CONVULSIVE EFFECT, AND PROCESS FOR THEIR PRODUCTION<br/>[FR] NOUVELLES 1-AR(ALK)YL-IMIDAZOLIN-2-ONES A EFFET ANTICONVULSIF CONTENANT UN RESTE AMINE BISUBSTITUE EN POSITION 4 ET PROCEDE PERMETTANT DE LES PREPARER
  申请人：ARZNEIMITTELWERK DRESDEN GMBH

  公开号：WO1997009314A1

  公开（公告）日：1997-03-13

  (DE) Antikonvulsiv wirkende Verbindungen der allgemeinen Formel (1), worin X = Wasserstoff, C1-C4-Alkyl, C1-C4-Alkoxy, Trifluormethyl, Halogen, R1 bzw. R2 = C1-C4-Alkyl, Cycloalkyl, Heteroalkyl bedeuten.(EN) Compounds with an anti-convulsive effect of general formula (1) in which X = hydrogen, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethyl, halogen and R1 or R2 = C1-C4 alkyl, cycloalkyl or heteroalkyl.(FR) L'invention concerne des composés à effet anticonvulsif de la formule générale (1) dans laquelle X désigne hydrogène, alkyle C1-C4, alcoxy C1-C4, trifluorométhyle, halogène, R1 et respectivement R2 désignent alkyle C1-C4, cycloalkyle, hétéroalkyle.

  (中文) 通式（1）的抗癫痫化合物，其中X = 氢，C1-C4烷基，C1-C4烷氧基，三氟甲基，卤素，R1或R2 = C1-C4烷基，环烷基或杂环烷基。
• Method of treating or preventing central nervous system disorders with compounds having selectivity benzodiazepine receptor
  申请人：Boehringer Ingelheim Vetmedica GmbH

  公开号：EP2027856A1

  公开（公告）日：2009-02-25

  The present invention relates to the use of 1-ar(alk)ylimidazolin-2-ones which contain a disubstituted amine radical in the 4-position for the treatment or prevention of central nervous system disorders including depression, anxiety, movement disorders, and especially dystonia, and psychotic disorders, and especially schizophrenia and psychotic symptoms associated to other mental disorders.

  本发明涉及在 4 位含有二取代胺基的 1-芳基咪唑啉-2-酮用于治疗或预防中枢神经系统疾病，包括抑郁症、焦虑症、运动障碍，尤其是肌张力障碍，以及精神障碍，尤其是精神分裂症和与其他精神障碍相关的精神症状。
• Method of treating or preventing central nervous system disorders with compounds having selectivity for the alpha 3 subunit of the benzodiazepine receptor
  申请人：Langen Barbara

  公开号：US20050032863A1

  公开（公告）日：2005-02-10

  The present invention relates to the use of 1-ar(alk)ylimidazolin-2-ones which contain a disubstituted amine radical in the 4-position for the treatment or prevention of central nervous system disorders including depression, anxiety, movement disorders, and especially dystonia, and psychotic disorders, and especially schizophrenia and psychotic symptoms associated to other mental disorders.

  本发明涉及在 4 位含有二取代胺基的 1-芳基咪唑啉-2-酮用于治疗或预防中枢神经系统疾病，包括抑郁症、焦虑症、运动障碍，尤其是肌张力障碍，以及精神障碍，尤其是精神分裂症和与其他精神障碍相关的精神症状。
• NEUE, ANTIKONVULSIV WIRKENDE 1-AR(ALK)YL-IMIDAZOLIN-2-ONE, DIE IN 4-STELLUNG EINEN DISUBSTITUIERTEN AMIN-REST ENTHALTEN, UND VERFAHREN ZU DEREN HERSTELLUNG
  申请人：Arzneimittelwerk Dresden GmbH

  公开号：EP0863880A1

  公开（公告）日：1998-09-16
• METHOD OF TREATING OR PREVENTING CENTRAL NERVOUS SYSTEM DISORDERS WITH COMPOUNDS HAVING SELECTIVITY FOR THE ALPHA 3 SUBUNIT OF THE BENZODIAZEPINE RECEPTOR
  申请人：elbion AG

  公开号：EP1646386A2

  公开（公告）日：2006-04-19