1,5-diphenyl-2-thiohydantoin | 194204-32-5

• 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: 1,5-diphenyl-2-thiohydantoin
• 英文别名: 1,5-diphenylthiohydantoin；1,5-Diphenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 194204-32-5
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: JACQWPJZGHCXBL-UHFFFAOYSA-N

物化性质

• 熔点：
  234.1-235.6 °C(Solv: ethanol (64-17-5))
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  α-溴苯乙酸甲酯 在 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.4h， 生成 1,5-diphenyl-2-thiohydantoin
  参考文献：
  名称：

  Baile; Mahajan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 6, p. 891 - 894

  摘要：

  DOI：

文献信息

• Microwave Assisted Synthesis of 1,5-Disubstituted Hydantoins and Thiohydantoins in Solvent-Free Conditions
  作者：Satya Paul、Mukta Gupta、Rajive Gupta、André Loupy

  DOI：10.1055/s-2002-19308

  日期：——

  1,5-Disubstituted hydantoins/thiohydantoins 3a-p have been synthesized in 8l-95% yield by a microwave-promoted solvent-free condensation of arylglyoxals 1 and phenylurea/thiourea 2 using PPE as a reaction mediator. This method can be extended towards the parallel synthesis of 3. The workup is simple and involves treatment with ice-cold water.

  1,5-二取代乙内酰脲/硫代乙内酰脲 3a-p 通过使用 PPE 作为反应介质，通过微波促进的芳基乙二醛 1 和苯基脲/硫脲 2 的无溶剂缩合以 8l-95% 的收率合成。这种方法可以扩展到 3 的平行合成。后处理简单，涉及用冰冷的水处理。
• Substituted 2-Thioxoimidazolidin-4-ones and Imidazolidine-2,4-diones as Fatty Acid Amide Hydrolase Inhibitors Templates
  作者：Giulio G. Muccioli、Nicola Fazio、Gerhard K. E. Scriba、Wolfgang Poppitz、Fabio Cannata、Jacques H. Poupaert、Johan Wouters、Didier M. Lambert

  DOI：10.1021/jm050977k

  日期：2006.1.1

  The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and 2-thioxoirnidazolidin-4-one derivatives was evaluated as FAAH inhibitors. Among these compounds, 3-substituted 5,5'-diplietiylimidazolidine-2,4-dione and 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one derivatives were previously described as CB, cannabinoid receptor ligands. In the present study, we synthesized several derivatives exhibiting interesting FAAH inhibitory activity and devoid of affinity for the CB, and CB, cannabinoid receptors. For instance, 3-heptyl-5,5'-diphenylimidazolidine-2,4-dione (14) and 5.5'-diphenyl-3-tetradecyl-2-thioxo-imidazolidin-4-one (46) showed pI(50) values of 5.12 and 5.94, respectively. In conclusion, it appears that even though several 3-substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one and 3-substituted 5.5'-diphenylimidazolidine-2,4-dione derivatives have been previously shown to behave as CB, cannabinoid receptor ligands, appropriate substitutions of these templates can result in FAAH inhibitors devoid of affinity for the cannabinoid receptors.