5-methyl-5-(4-morpholinophenyl)imidazolidine-2,4-dione | 21231-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 5-methyl-5-(4-morpholinophenyl)imidazolidine-2,4-dione
• 英文别名: Hydantoin von E；5-methyl-5-(4-morpholin-4-yl-phenyl)-imidazolidine-2,4-dione；5-Methyl-5-(4-morpholin-4-ylphenyl)imidazolidine-2,4-dione
• CAS: 21231-66-3
• 化学式: C₁₄H₁₇N₃O₃
• 分子量: 275.307
• InChiKey: HJZOCXZAOPNUHE-UHFFFAOYSA-N

物化性质

• 密度：
  1.253±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-5-(4-morpholinophenyl)imidazolidine-2,4-dione 、 2-氯-2',4'-二氟苯乙酮 在 potassium carbonate 作用下， 以62%的产率得到3-(2-(2,4-difluorophenyl)-2-oxoethyl)-5-methyl-5-(4-morpholinophenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

  摘要：

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

  DOI：

  10.1021/acs.jmedchem.8b01356
• 作为产物：
  描述：

  4-(4-吗啉基)苯乙酮 、 potassium cyanide 、 ammonium carbonate 以 乙醇 、 水 为溶剂， 反应 18.0h， 以35%的产率得到5-methyl-5-(4-morpholinophenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

  摘要：

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

  DOI：

  10.1021/acs.jmedchem.8b01356