2-ethyl-4-phenyl-[1,2,4]thiadiazolidine-3,5-dione | 7707-42-8

• 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: 2-ethyl-4-phenyl-[1,2,4]thiadiazolidine-3,5-dione
• 英文别名: 2-ethyl-4-phenyl-[1,2,4]thiazolidine-3,5-dione；2-Aethyl-4-phenyl-<1,2,4>thiadiazolidin-3,5-dion；2-Ethyl-4-phenyl-1,2,4-thiadiazolidine-3,5-dione
• CAS: 7707-42-8
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: XXSGUVAYNNBBFW-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  318.1±25.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-chloro-N-phenylisothiocarbamoyl chloride 在 水 作用下， 生成 2-ethyl-4-phenyl-[1,2,4]thiadiazolidine-3,5-dione
  参考文献：
  名称：

  Ottmann,G.; Hooks,H., Angewandte Chemie, 1966, vol. 78, p. 681

  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.
• N-Chlorosuccinimide is a convenient oxidant for the synthesis of 2,4-disubstituted 1,2,4-thiadiazolidine-3,5-diones
  作者：Shama Nasim、Peter A. Crooks

  DOI：10.1016/j.tetlet.2008.10.136

  日期：2009.1

  N-Chlorosuccinimide has been identified as a convenient and safe alternative oxidant for the oxidative condensation of isothiocyanates and isocyanates to afford 1,2,4-thiadiazolidine-3,5-diones. (C) 2008 Elsevier Ltd. All rights reserved.
• Slomczynska, Urszula; Barany, George, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 241 - 246
  作者：Slomczynska, Urszula、Barany, George

  DOI：——

  日期：——
• SLOMCZYNSKA, U.;BARANY, G., J. HETEROCYCL. CHEM., 1984, 21, N 1, 241-246
  作者：SLOMCZYNSKA, U.、BARANY, G.

  DOI：——

  日期：——
• [EN] THE USE OF 1, 2, 4-THIADIAZOLIDINE-3, 5-DIONES AS PPAR ACTIVATORS<br/>[FR] UTILISATION DE 1, 2, 4-THIADIAZOLIDINE-3, 5-DIONES EN TANT QU'ACTIVATEURS DE PPAR
  申请人：NEUROPHARMA SA

  公开号：WO2006045581A1

  公开（公告）日：2006-05-04

  [EN] The invention is related to the use of a family of structurally distinct compounds having a thiadiazolidine heterocycle core which are potent PPAR ligands and have good pharmacological properties, for the treatment of diseases or conditions that require PPAR activation or are PPAR mediated.
  [FR] L'invention concerne l'utilisation d'une famille de composés de structures distinctes possédant un noyau hétérocyclique de thiadiazolidine et constituant des ligands puissants de PPAR, tout en possédant de bonnes propriétés pharmacologiques. Ces composés servent à traiter des maladies ou des états nécessitant l'activation de PPAR ou dans lesquels PPAR jouent un rôle d'intermédiaire.