(5Z)-5-[(4-phenylphenyl)methylidene]imidazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5Z)-5-[(4-phenylphenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: QIYDZMXXQWNWHJ-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  海因 、 对苯基苯甲醛 在 碳酸氢钠 、 C.I.酸性橙108 作用下， 以 乙醇 为溶剂， 以70.6%的产率得到(5Z)-5-[(4-phenylphenyl)methylidene]imidazolidine-2,4-dione
  参考文献：
  名称：

  Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study

  摘要：

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.

  DOI：

  10.1021/jm030450c

文献信息

• Process for producing 4-biphenylylacetic acid
  申请人：LEDERLE (JAPAN) LTD.

  公开号：EP0212617B1

  公开（公告）日：1989-01-11