3-benzyl-5,5-diphenyl-imidazolidine-2,4-dione | 34657-67-5

• 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: 3-benzyl-5,5-diphenyl-imidazolidine-2,4-dione
• 英文别名: 3-benzyl-5,5-diphenylhydantoin；3-Benzyl-5,5-diphenyl-imidazolidin-2,4-dion；3-Benzyl-5,5-diphenyl-hydantoin；3-Benzyl-5.5-diphenyl-hydantoin；3-Benzyl-5,5-diphenylimidazolidine-2,4-dione
• CAS: 34657-67-5
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: IKGOBAYQCFFAGE-UHFFFAOYSA-N

物化性质

• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-5,5-diphenyl-imidazolidine-2,4-dione 以57%的产率得到
  参考文献：
  名称：

  VIDA J. A.; ODEA M. N.; SAMOUR. S. M., J. MED. CHEM. , 1975, 18, NO 4, 383-385

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-bis-methylsulfanyl-4,4-diphenyl-4H-imidazole 在 盐酸 、 sodium hydroxide 、 溶剂黄146 作用下， 生成 3-benzyl-5,5-diphenyl-imidazolidine-2,4-dione
  参考文献：
  名称：

  79.硫代乙内酰脲。第三部分 5：5-二取代乙内酰脲的N-和S-甲基衍生物及其一硫代和二硫代类似物

  摘要：

  DOI：

  10.1039/jr9500000354

文献信息

• Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization / cleavage step
  作者：Bruce A. Dressman、Larry A. Spangle、Stephen W. Kaldor

  DOI：10.1016/0040-4039(95)02395-x

  日期：1996.2

  An 800 compound hydantoin library has been constructed using a diverse set of 20 amino acids and over 80 primary amines. Amino acids were attached via their N-termini to hydroxymethyl polystyrene using a carbamate linker. Bound amino acids were converted to their corresponding amides and then cyclized under basic conditions to give hydantoins in high purities.

  已使用20种氨基酸和80多种伯胺构成了800个化合物的乙内酰脲文库。使用氨基甲酸酯连接基，氨基酸通过其N-末端连接至羟甲基聚苯乙烯。将结合的氨基酸转化为它们相应的酰胺，然后在碱性条件下环化以得到高纯度的乙内酰脲。
• Structure-activity relationships of 3-substituted-5,5- diphenylhydantoins as potential antiproliferative and antimicrobial agents
  作者：Nemanja Trisovic、Bojan Bozic、Ana Obradovic、Olgica Stefanovic、Snezana Markovic、Ljiljana Comic、Biljana Bozic、Gordana Uscumlic

  DOI：10.2298/jsc110314143t

  日期：——

  A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evaluated to determine structure-activity relationships. Almost all of the compounds exhibited statistically significant antiproliferative effects at a concentration of 100 ?M, while the derivative bearing a benzyl group was active even at lower concentrations. Moreover, their in vitro antibacterial activities against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and clinical isolates of Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus aureus were evaluated. Only the 3-iso-propyl and 3-benzyl derivatives showed weak antibacterial activities against the Gram-positive bacterium E. faecalis and the Gram-negative bacteria E. coli ATCC 25922 and E. coli.

  合成了十二种 3-取代-5,5-二苯基海因系列、 包括一些已在文献中报道过其抗惊厥活性的化合物。 文献中已有报道。评估了它们对 HCT-116 人结肠癌细胞的抗增殖活性，以确定其作用机制。 结肠癌细胞的抗增殖活性进行了评估，以确定结构-活性关系。 关系。几乎所有化合物都表现出了统计学意义上的 的抗增殖作用，而带有苄基的衍生物在浓度为 100? 而带有苄基的衍生物即使在较低浓度下也具有活性。 此外，它们在体外对大肠杆菌 大肠杆菌 ATCC 25922、金黄色葡萄球菌 ATCC 25923 和临床分离的 大肠杆菌、奇异变形杆菌、铜绿假单胞菌、粪肠球菌和葡萄球菌的体外抗菌活性。 粪肠球菌和金黄色葡萄球菌进行了评估。只有 3-异丙基和 3-苄基衍生物对革兰氏阳性菌大肠杆菌和金黄色葡萄球菌表现出微弱的抗菌活性。 革兰氏阳性菌粪肠球菌和革兰氏阴性菌大肠杆菌 ATCC 25922 和 E. coli.
• 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。
• Solvent Effects on the Structure-Activity Relationship of Pharmacological Active 3-Substituted-5,5-Diphenylhydantoins
  作者：Nebojša Banjac、Gordana Ušćumlić、Nataša Valentić、Dušan Mijin

  DOI：10.1007/s10953-007-9153-2

  日期：2007.7

  Absorption spectra of eight 3-substituted-5,5-diphenylhydantoins have been recorded in fourteen solvents in the range 200–400 nm. The effect of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions are analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by the calculation of log 10 P values with the Advanced Chemistry Development Software. The calculated values of log 10 P were correlated with the ratio of the contributions of specific solvent interactions, and, by employing the linear dependence thus obtained, the pharmacological activity of the studied hydantoin derivatives is discussed.

  已在 200-400 nm 范围内的 14 种溶剂中记录了 8 种 3-取代-5,5-二苯基乙内酰脲的吸收光谱。利用 Kamlet 和 Taft 提出的线性溶剂化能量关系 (LSER) 概念分析了溶剂偶极/极化性和溶剂/溶质氢键相互作用的影响。通过使用高级化学开发软件计算 log 10 P 值来估计所研究的乙内酰脲的亲脂活性。 log 10 P的计算值与特定溶剂相互作用的贡献比相关，并且通过利用由此获得的线性依赖性，讨论了所研究的乙内酰脲衍生物的药理活性。
• Oligomer-containing hydantoin compounds
  申请人：Riggs-Sauthier Jennifer

  公开号：US09540330B2

  公开（公告）日：2017-01-10

  The invention relates to (among other things) oligomer-containing hydantoin compounds. A compound of the invention, when administered by any of a number of administration routes, exhibits one or more advantages over corresponding compounds lacking the oligomer.

  本发明涉及（除其他事项外）含寡聚物的海因图因化合物。本发明的化合物在通过多种给药途径之一给予时，相对于缺乏寡聚物的相应化合物，表现出一种或多种优点。