4-ethyl-2-isopropyl-1,2,4-thiadiazolidine-3,5-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethyl-2-isopropyl-1,2,4-thiadiazolidine-3,5-dione
• 英文别名: 4-Ethyl-2-isopropyl-1,2,4-thiadiazolidin-3,5-dione；4-ethyl-2-propan-2-yl-1,2,4-thiadiazolidine-3,5-dione
• 化学式: C₇H₁₂N₂O₂S
• 分子量: 188.25
• InChiKey: DLGHVUQYPMHDTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  5-chloro-4-ethyl-2-isopropyl-3-oxo-1,2,4-thiadiazolium chloride 在 air 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以19%的产率得到4-ethyl-2-isopropyl-1,2,4-thiadiazolidine-3,5-dione
  参考文献：
  名称：

  Arylimino-1,2,4-噻二唑烷酮类：钾通道开放剂的新家族。

  摘要：

  使用从噻二唑并吡啶鎓氯化物开始的有效合成，制备了一系列芳基-1,2,4-噻二唑烷。所有化合物在大鼠门静脉中均显示出平滑的肌肉松弛特性。在高度去极化的条件下不同的行为以及格列本脲对生物效应的降低表明，阿里木氨基-1,2,4-噻二唑啉酮-3-酮可能至少部分通过K +诱导的血管平滑细胞超极化作用。

  DOI：

  10.1016/s0968-0896(97)00077-1

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。
• Synthesis and Potential Muscarinic Receptor Binding and Antioxidant Properties of 3-(Thiadiazolyl)pyridine 1-Oxide Compounds
  作者：Ana Martinez、Diana Alonso、Ana Castro、Vicente J. Arán、Ignasi Cardelús、Josep E. Baños、Albert Badia

  DOI：10.1002/(sici)1521-4184(19996)332:6<191::aid-ardp191>3.0.co;2-x

  日期：1999.6

  The synthesis of two different series of 3‐(thiadiazolyl)pyridine 1‐oxides containing 1,2,5‐ and 1,2,4‐thiadiazole moiety respectively is described. The potential muscarinic receptor binding together with the antioxidant properties of the new compounds were evaluated.

  描述了分别含有 1,2,5- 和 1,2,4-噻二唑部分的两种不同系列的 3-（噻二唑基）吡啶 1-氧化物的合成。评估了潜在的毒蕈碱受体结合以及新化合物的抗氧化特性。
• 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.
• N-Benzylpiperidine derivatives of 1,2,4-thiadiazolidinone as new acetylcholinesterase inhibitors
  作者：Ana Martinez、Enrique Fernandez、Ana Castro、Santiago Conde、Isabel Rodriguez-Franco、Josep-Eladı́ Baños、Albert Badia

  DOI：10.1016/s0223-5234(00)01166-1

  日期：2000.10

  A new family of 1,2,4-thiadiazolidinone derivatives containing the N-benzylpiperidine fragment has been synthesised. The acetylcholinesterase (AChE) inhibitory activity of all compounds was measured using Ellman's method and some of them turned out to be as potent as tacrine. Furthermore, compound 13 was as active as tacrine in reversing the blockade induced by tubocurarine at rat neuromuscular junction. Additionally, receptor binding studies provided new lead compounds for further development of alpha (2)-adrenergic and sigma-receptor antagonists. Molecular dynamic simulation using X-ray crystal structure of AChE from Torpedo californica was used to explain the possible binding mode of these new compounds. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• US6872737B2
  申请人：——

  公开号：US6872737B2

  公开（公告）日：2005-03-29