3,5-diphenyl-2-thioxoimidazolidin-4-one | 61815-22-3

• 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: 3,5-diphenyl-2-thioxoimidazolidin-4-one
• 英文别名: 3,5-Diphenyl-2-thiohydantoin；3,5-Diphenyl-2-thioxo-imidazolidin-4-on；3,5-diphenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 61815-22-3；138088-51-4；138088-52-5
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: NOOPLYYILFCGRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  232.1-233.6 °C(Solv: water (7732-18-5))
• 沸点：
  404.2±48.0 °C(Predicted)
• 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

• 作为反应物：
  描述：

  3,5-diphenyl-2-thioxoimidazolidin-4-one 在 sodium hydroxide 、 氧气 作用下， 生成 1,4,1',4'-tetraphenyl-2,2'-dithioxo-octahydro-[4,4']biimidazolyl-5,5'-dione
  参考文献：
  名称：

  468.硫代乙内酰脲。第四部分 在碱性溶液中被分子氧氧化

  摘要：

  DOI：

  10.1039/jr9590002327
• 作为产物：
  描述：

  2-phenyl-2-(phenylcarbamothioylamino)acetic acid 在 盐酸 作用下， 以 水 为溶剂， 生成 3,5-diphenyl-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

  摘要：

  A series of substituted (+/-)3,5-diphenyl-2-thioxoimidazolin-4-ones was synthesized in order to design new type-2 cyclooxygenase (COX-2) inhibitors. This study has led to Molecules which completely inhibit human recombinant COX-2 at 50 mu M. Molecular modelling highlighted drug interactions with the active site of both cyclooxygenases and suggested modifications to enhance the selectivity of the compounds. In human blood, COX-2 expression was then induced by LPS, and the inhibitory potency of these drugs was disappointing. This weak activity was attributed to a poor aqueous stability of these imidazolidinones Substituted by two aryl in position 3 and 5 (15 min < t(1/2) < 130 min). The improvement of the stability of this heterocycle Could generate a novel template to treat COX-associated diseases Such as arthritis, rheumatoid polyarthritis and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.005

文献信息

• An Efficient Method for Synthesis of Thiohydantoins with a-Amino Esters Under Microwave Irradiation
  作者：Yanmei Zhao、Zhouyu Wang、Zhenju Jiang、Hualin Feng、Li Liu、Ju Wang

  DOI：10.14233/ajchem.2014.16119

  日期：——

  An efficient and simple way for synthesis of thiohydantoins is reported. In the absence of any additional catalysts, a series of thiohydantoins were synthesized with amino esters and isothiocyanates in aqueous medium under microwave irradiation. Excellent isolated yields (up to 98 %) were obtained under mild conditions.

  报告采用了一种高效而简单的方法合成硫代海因。在没有任何额外催化剂的情况下，在微波辐照下，在水介质中用氨基酯和异硫氰酸盐合成了一系列硫代海因。在温和的条件下，获得了极佳的分离产率（高达 98%）。
• Chiral Recognition of Chiral (Hetero)Cyclic Derivatives Probed by Tetraaza Macrocyclic Chiral Solvating Agents via ¹H NMR Spectroscopy
  作者：Yu Wang、Hongmei Zhao、Chunxia Yang、Lixia Fang、Li Zheng、Hehua Lv、Pericles Stavropoulos、Lin Ai、Jiaxin Zhang

  DOI：10.1021/acs.analchem.3c05395

  日期：2024.4.2

  of 1H NMR spectroscopy. In this paper, enantiomers of thiohydantoin derivatives, representing typical five-membered N,N-heterocycles, have been synthesized and utilized for assignment of absolute configuration and analysis of enantiomeric excess. All enantiomers have been successfully differentiated with the assistance of novel tetraaza macrocyclic chiral solvating agents (TAMCSAs) by 1H NMR spectroscopy

  在手性识别领域，手性环状有机化合物，尤其是杂环有机化合物，很少受到关注，很少通过 1H NMR 波谱作为手性底物进行研究。在本文中，已经合成了硫代乙内酰脲衍生物的对映异构体，代表典型的五元 N，N-杂环，并用于分配绝对构型和对映体过量的分析。在新型四氮大环手性溶剂化剂 （TAMCSA） 的帮助下，通过 1H NMR 波谱成功区分了所有对映异构体。令人惊讶的是，已经观察到底物的 NH 质子前所未有的非等效化学位移值（高达 2.052 ppm），这是对映异构体评估的新里程碑。为了更好地了解主体和客体之间的分子间相互作用，研究了 （S）-G1 和 （R）-G1 与 TAMCSA 1a 的 Job 图和理论计算，并揭示了非对映异构体之间的显着几何差异。为了评估本系统在分析手性衬底的光学纯度方面的实际应用，在具有代表性的 TAMCSA （1a） 存在下，具有不同光学成分的典型衬底 （G1） 的对映体过量可以根据
• 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.
• Synthesis of new 2,5-diamino-1,3-thiazole and 2-thiohydantoin derivatives by condensation of N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides with thioureas
  作者：A. G. Balya、A. N. Chernega、S. A. But、A. N. Vasilenko、V. S. Brovarets、B. S. Drach

  DOI：10.1134/s1070363208070268

  日期：2008.7

  N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides react under mild conditions with thiourea, N-alkyl-and N-arylthioureas, and various N,N'-disubstituted thioureas, following the Hantzsch reaction scheme. The reactions are selective, and the resulting 2,5-diamino-1,3-thiazole derivatives undergo recyclization acid followed by hydrolysis to give substituted 2-thiohydantoins on heating with hydrochloric acid in ethanol.
• Kossel, Chemische Berichte, 1891, vol. 24, p. 4154
  作者：Kossel

  DOI：——

  日期：——