1,2-dibenzoyl-4-phenyl-1,2,4-triazolidine-3,5-dione | 63412-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-dibenzoyl-4-phenyl-1,2,4-triazolidine-3,5-dione
• CAS: 63412-64-6
• 化学式: C₂₂H₁₅N₃O₄
• 分子量: 385.379
• InChiKey: IRPSPSCQDZDJAT-UHFFFAOYSA-N

物化性质

• 熔点：
  276-280 °C
• 沸点：
  528.5±33.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苯基脲唑 以64%的产率得到
  参考文献：
  名称：

  CAPUANO L.; MUELLER K., CHEM. BER. , 1977, 110, NO 5, 1691-1698

  摘要：

  DOI：

文献信息

• SAR and 3D-QSAR Studies on Thiadiazolidinone Derivatives:  Exploration of Structural Requirements for Glycogen Synthase Kinase 3 Inhibitors
  作者：Ana Martinez、Mercedes Alonso、Ana Castro、Isabel Dorronsoro、J. Luis Gelpí、F. Javier Luque、Concepción Pérez、Francisco J. Moreno

  DOI：10.1021/jm040895g

  日期：2005.11.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) are described as the first ATP-noncompetitive GSK-3 inhibitors. Following an SAR study about TDZD, different structural modifications in the heterocyclic ring aimed to test the influence of each heteroatom on the biological study are here reported here. Various compounds such as hydantoins, dithiazolidindiones, rhodanines, maleimides, and triazoles were synthesized and screened as GSK-3 inhibitors. After an extensive SAR study among these different heterocyclic families, TDZDs have been revealed as a privileged scaffold for the selective inhibition of GSK-3. A CoMFA analysis was also performed highlighting the molecular electrostatic field interaction in the interaction of TDZDs with GSK-3. Moreover, first mapping studies indicate two binding modes which in turn might imply relevant differences in the mechanism that underly the inhibitory activity of TDZDs.
• Structure and Conformations of Monoacyl and Diacyl 1,2,4-Triazolidine-3,5-diones
  作者：Robert A. Izydore、Anthony A. Ribeiro、Iris H. Hall

  DOI：10.1021/jo951965h

  日期：1996.1.1

  A series of monoacyl and diacyl 1,2,4-triazolidine-3,5-diones substituted at position 4 with either a phenyl or a tert-butyl group was prepared. Both acetyl and benzoyl groups were utilized as the acyl substituents. The diacylated compounds containing one or two acetyl groups were somewhat unstable to moisture. The acylated compounds were studied by H-1, C-13 and N-15 NMR spectroscopy and X-ray crystallography to determine if they were acylated on nitrogen or ring carbonyl oxygen. The results indicated that the acylations occurred on nitrogen. The NMR spectra and molecular modeling computations were used to assign conformations to several of the diacylated compounds.