2,4-diethyl-1,2,4-thiadiazolidine-3-thione-5-one | 98484-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-diethyl-1,2,4-thiadiazolidine-3-thione-5-one
• 英文别名: 2,4-diethyl-3-thioxo-[1,2,4]thiadiazolidin-5-one；2,4-Diaethyl-3-thioxo-[1,2,4]thiadiazolidin-5-on；2,4-diethyl-5-oxo-1,2,4-thiadiazolidine-3-thione；2,4-Diethyl-3-sulfanylidene-1,2,4-thiadiazolidin-5-one
• CAS: 98484-44-7
• 化学式: C₆H₁₀N₂OS₂
• 分子量: 190.29
• InChiKey: LDHHNMNHSWWSNP-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44 °C
• 沸点：
  239.6±23.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-ethyl-5-ethylimino-1,2,4-dithiazolidin-3-one 以 三溴甲烷 为溶剂， 生成 2,4-diethyl-1,2,4-thiadiazolidine-3-thione-5-one
  参考文献：
  名称：

  Selective formation of five-membered heterocyclic products by anodic oxidation of alkyl isothiocyanates (RNCS) in dichloromethane and their thermal isomerization and decomposition

  摘要：

  DOI：

  10.1021/jo00243a028

文献信息

• First Non-ATP Competitive Glycogen Synthase Kinase 3 β (GSK-3β) Inhibitors:  Thiadiazolidinones (TDZD) as Potential Drugs for the Treatment of Alzheimer's Disease
  作者：Ana Martinez、Mercedes Alonso、Ana Castro、Concepción Pérez、Francisco J. Moreno

  DOI：10.1021/jm011020u

  日期：2002.3.1

  Glycogen synthase kinase 3beta (GSK-3beta) has a central role in Alzheimer's disease (AD). Selective inhibitors which avoid tau hyperphosphorylation may represent an effective therapeutical approach to the AD pharmacotherapy and other neurodegenerative disorders. Here, we describe the synthesis, biological evaluation, and SAR of the small heterocyclic thiadiazolidinones (TDZD) as the first non-ATP competitive inhibitor of GSK-3beta. Their synthesis is based on the reactivity of sulfenyl chlorides. In GSK-3beta assays, TDZD derivatives showed IC50 values in the micromolar range, whereas in other protein kinases assays they were devoid of any inhibitory activity. SAR studies allowed the identification of the key structural features. Finally, a possible enzymatic binding mode is proposed.
• Anodic oxidation of alkyl isocyanates and their thio derivatives in acetonitrile
  作者：James Y. Becker、Baruch Zinger、Shimon Yatziv

  DOI：10.1021/jo00389a026

  日期：1987.6
• Tittelbach, Franz, Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 2, p. 180 - 190
  作者：Tittelbach, Franz

  DOI：——

  日期：——
• BECKER J. Y.; ZINGER B.; YATZIV S., J. ORG. CHEM., 52,(1987) N 13, 2783-2789
  作者：BECKER J. Y.、 ZINGER B.、 YATZIV S.

  DOI：——

  日期：——
• Synthesis of 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-trithione through ethyl-(4-ethyl-5-thioxo-[1,2,4]-dithiazolidin-3-ylidene)ammonium oxopentachlorotungstate(VI) hydrolysis and the dimroth rearrangement in it on heating
  作者：N. A. Ovchinnikova、A. E. Sinyakov、S. G. Sakharov、A. E. Gekhman、Yu. N. Mikhailov、A. S. Kanishcheva

  DOI：10.1134/s0020168513090112

  日期：2013.9

  We demonstrate that the previously synthesized product of ethyl isothiocyanate insertion into tungsten hexachloride, WCl5N(Et)C(S)N(Et)C(S)Cl}, whose partial hydrolysis yields N(Et)C(S)-S-S-C=NH(Et)}[WOCl5] (I), can be used as a source of biologically active heterocyclic compounds. H-1 and C-13 NMR and gas chromatography-mass spectrometry data show that reaction of I with a saturated aqueous Na2CO3 solution yields a number of thiazolidine heterocycles, mostly 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-trithione. The thermal Dimroth rearrangement leads to the formation of 2,4-diethyl-[1,2,4]-dithiazolidin-3,5-dithione and the products of partial hydrolysis of both heterocycles: 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-on and 2,4-diethyl-3-thioxo-[1,2,4]-dithiazolidin-5-on.