2-Methyl-4-phenyl-1,2,4-thiadiazolidin-3,5-dion | 38958-66-6

• 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: 2-Methyl-4-phenyl-1,2,4-thiadiazolidin-3,5-dion
• 英文别名: 2-methyl-4-phenyl-[1,2,4]thiadiazolidine-3,5-dione；4-phenyl-2-methyl-1,2,4-thiadiazolidin-3,5-dione；4-Phenyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione；2-methyl-4-phenyl-1,2,4-thiadiazolidine-3,5-dione
• CAS: 38958-66-6
• 化学式: C₉H₈N₂O₂S
• 分子量: 208.241
• InChiKey: LSXPXEJAKMFTTI-UHFFFAOYSA-N

物化性质

• 熔点：
  174-179 °C
• 沸点：
  303.8±25.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-甲基-3-苯基硫脲 在 三乙胺 、 benzohydroximoyl chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-Methyl-4-phenyl-1,2,4-thiadiazolidin-3,5-dion
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Enzyme inhibitors
  申请人：——

  公开号：US20030195238A1

  公开（公告）日：2003-10-16

  Compounds of general formula (I): 1 where A, E, G, X, Y and the bond - - - take various meanings are of use in the preparation of a pharmaceutical formulation, for example in the treatment of a disease in which GSK-3 is involved, including Alzheimer's disease or the non-dependent insulin diabetes mellitus, or hyperproliferative disease such as cancer, displasias or metaplasias of tissue, psoriasis, arteriosclerosis or restenosis.

  通式（I）的化合物： 其中A、E、G、X、Y和键- - - 取不同含义，在制备药物配方中有用，例如在治疗涉及GSK-3的疾病中，包括阿尔茨海默病或非依赖胰岛素糖尿病，或高增殖性疾病，如癌症、组织发育不良或异型增生、银屑病、动脉硬化或再狭窄症。
• 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.
• 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：——
• US6872737B2
  申请人：——

  公开号：US6872737B2

  公开（公告）日：2005-03-29