ethyl(2-ethyl-3-oxo-4-phenyl-1,2,4-thiadiazolidin-5-ylidene)urea | 139407-52-6

• 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: ethyl(2-ethyl-3-oxo-4-phenyl-1,2,4-thiadiazolidin-5-ylidene)urea
• 英文别名: Thiadiazolidinone (TDZD) deriv. 26；(3Z)-1-ethyl-3-(2-ethyl-3-oxo-4-phenyl-1,2,4-thiadiazolidin-5-ylidene)urea
• CAS: 139407-52-6
• 化学式: C₁₃H₁₆N₄O₂S
• 分子量: 292.362
• InChiKey: XKPDTDAOVRTTRA-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl(2-ethyl-3-oxo-4-phenyl-1,2,4-thiadiazolidin-5-ylidene)urea 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以50%的产率得到2-Ethyl-5-imino-4-phenyl-[1,2,4]thiadiazolidin-3-one
  参考文献：
  名称：

  First Non-ATP Competitive Glycogen Synthase Kinase 3 β (GSK-3β) Inhibitors:  Thiadiazolidinones (TDZD) as Potential Drugs for the Treatment of Alzheimer's Disease

  摘要：

  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.

  DOI：

  10.1021/jm011020u
• 作为产物：
  描述：

  N-苯基-1,2,3,4-三噻唑-5-胺 、 异氰酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 70.0h， 以81%的产率得到ethyl(2-ethyl-3-oxo-4-phenyl-1,2,4-thiadiazolidin-5-ylidene)urea
  参考文献：
  名称：

  The reactions of 5-amino-1,2,3,4-thiatriazoles with isocyanates

  摘要：

  The reaction of 5-(arylamino)-1,2,3,4-thiatriazoles 1 with isocyanates initially gives 1,2,3,4-thiatriazol-5-ylureas 3 which can be isolated when the aryl group has o-alkyl substituents. Compounds 3 rearrange to 21 in the presence of triethylamine and then react with the second equivalent of isocyanate to give (4-aryl-2-alkyl-3-oxo-1,2,4-thiadiazolidin-5-ylidene)ureas 12 rather than the (3-oxo-DELTA(4)-1,2,4-thiadiazolin-5-yl)ureas 7 which had been proposed previously.1 The latter compounds, prepared from 8 and isocyanates, also rearrange to 12. Mechanisms incorporating these observations are proposed (Schemes IV and VI). The structure of 12 was confirmed by single-crystal X-ray analysis of [4-(2,6-dimethylphenyl)-2-methyl-3-oxo-1,2,4-thiadiazolidin-5-ylidene]methylurea 12baa.

  DOI：

  10.1021/jo00032a014