4-[(4-ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)methyl]-benzonitrile | 778619-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-[(4-ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)methyl]-benzonitrile
• 英文别名: 4-[(4-Ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)methyl]benzonitrile；4-[(4-ethyl-2,5-dioxo-4-phenylimidazolidin-1-yl)methyl]benzonitrile
• CAS: 778619-05-9
• 化学式: C₁₉H₁₇N₃O₂
• 分子量: 319.363
• InChiKey: WEFXGNLEJPOLGX-UHFFFAOYSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氰基氯苄 、 5-乙基-5-苯基海因 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到4-[(4-ethyl-2,5-dioxo-4-phenyl-1-imidazolidinyl)methyl]-benzonitrile
  参考文献：
  名称：

  New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations

  摘要：

  Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.

  DOI：

  10.1007/s00706-013-1149-6

文献信息

• New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
  作者：Sleem Hmuda、Nemanja Trišović、Jelena Rogan、Dejan Poleti、Željko Vitnik、Vesna Vitnik、Nataša Valentić、Biljana Božić、Gordana Ušćumlić

  DOI：10.1007/s00706-013-1149-6

  日期：2014.5

  Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.