3-苄基-5-乙基-5-苯基-2,4-咪唑烷二酮 | 93879-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-苄基-5-乙基-5-苯基-2,4-咪唑烷二酮
• 英文名称: (+/-)-N-3-benzyl-Nirvanol
• 英文别名: (+)-N-3-benzylnirvanol；N-3-benzylnirvanol；N-benzylnirvanol；benzylnirvanol；benzynirvanol；3-benzyl-5-ethyl-5-phenyl-imidazolidine-2,4-dione；3-Benzyl-5-ethyl-5-phenylimidazolidine-2,4-dione
• CAS: 93879-40-4
• 化学式: C₁₈H₁₈N₂O₂
• mdl: MFCD07353973
• 分子量: 294.353
• InChiKey: ZMZDHUHMXXALFX-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136°C
• 密度：
  1.190±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  氯化苄 、 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62%的产率得到3-苄基-5-乙基-5-苯基-2,4-咪唑烷二酮
  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

• Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins
  作者：Sleem F. Hmuda、Nemanja P. Trišović、Nataša V. Valentić、Gordana S. Ušćumlić

  DOI：10.1007/s10953-010-9641-7

  日期：2011.2

  moderate electron-donating and electron-withdrawing substituents at the benzyl moiety, while the strong electron-withdrawing substituent (NO2) significantly modifies the solvation characteristics of the molecule. The paper clearly demonstrates how the solvatochromic comparison method may be applied to estimate the contributions of various modes of solvation to the pharmaceutically relevant properties of

  合成了两个系列的 3-(4-取代苄基)-5-乙基-5-苯基-和 3-(4-取代苄基)-5,5-二苯基乙内酰脲, 并在 200-400 范围内记录了它们的紫外吸收光谱nm 在不同极性的选定溶剂中。通过 Kamlet 和 Taft 的线性溶剂化能量关系 (LSER) 方法分析溶剂偶极/极化率和溶剂/溶质氢键相互作用对光谱位移的影响。讨论了氢键相互作用与所研究化合物的亲脂性和血脑渗透性之间的定量关系。对于苄基部分的中等给电子和吸电子取代基，获得了令人满意的线性相关性，而强吸电子取代基（NO2）显着改变了分子的溶剂化特性。该论文清楚地展示了如何应用溶剂化变色比较方法来估计各种溶剂化模式对这些新合成的乙内酰脲衍生物的药学相关特性的贡献。
• DE611057
  申请人：——

  公开号：——

  公开（公告）日：——
• CH169585
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.