N-ethyl-S-chloroisothiocarbamoyl chloride | 5180-27-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 亚胺酰卤
• 英文名称: N-ethyl-S-chloroisothiocarbamoyl chloride
• 英文别名: ethyliminochloromethylsulfenyl chloride；N-ethyl-carbonochloridimidic hypochlorous thioanhydride；chloro-(chloro-ethylimino-methyl)-sulfane；N-Ethyl-S-chlor-isothiocarbamoylchlorid
• CAS: 5180-27-8
• 化学式: C₃H₅Cl₂NS
• 分子量: 158.051
• InChiKey: LLDHXOWIARPVIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  7.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-ethyl-S-chloroisothiocarbamoyl chloride 、 异氰酸苄酯 在 水 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-benzyl-4-ethyl-[1,2,4]thiadiazolidine-3,5-dione
  参考文献：
  名称：

  THIADIAZOLIDINEDIONES AS GSK-3 INHIBITORS

  摘要：

  本发明涉及新型噻二唑烷二酮类化合物，其化学公式为(I)，或任何药学上可接受的盐、溶剂化物或前药，以及其在治疗糖原合酶激酶3 (GSK-3)参与的疾病中的应用，特别是神经退行性疾病、炎症和自身免疫疾病以及心血管障碍。此外，还提供了制备此类化合物的方法，以及包含它们的药物组合物。

  公开号：

  US20150038538A1
• 作为产物：
  描述：

  异硫氰酸乙酯 在 氯 作用下， 以 正己烷 为溶剂， 生成 N-ethyl-S-chloroisothiocarbamoyl chloride
  参考文献：
  名称：

  3-（噻二唑基）吡啶 1-氧化物化合物的合成和潜在毒蕈碱受体结合和抗氧化特性

  摘要：

  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。

  DOI：

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

文献信息

• Synthesis and Biological Evaluation of Tacrine-Thiadiazolidinone Hybrids as Dual Acetylcholinesterase Inhibitors
  作者：Isabel Dorronsoro、Diana Alonso、Ana Castro、Maria del Monte、Esther García-Palomero、Ana Martínez

  DOI：10.1002/ardp.200400919

  日期：2005.1

  The synthesis of tacrine‐thiadiazolidinone hybrids is described. These compounds are designed as dual acetylcholinesterase inhibitors binding simultaneously to the peripheral and catalytic sites of the enzyme. All tested compounds exhibit significant AChE inhibitory activity. Competition assays using propidium as reference of selective ligand for the peripheral anionic site on acetylcholinesterase indicates

  描述了他克林-噻二唑烷酮杂化物的合成。这些化合物被设计为双乙酰胆碱酯酶抑制剂，同时与酶的外周和催化位点结合。所有测试的化合物都表现出显着的 AChE 抑制活性。使用丙锭作为乙酰胆碱酯酶外周阴离子位点的选择性配体参考的竞争分析表明设计的化合物对外周位点的影响。它们可以被视为优化阿尔茨海默病调节剂的新线索。
• 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.
• Ottmann,G.; Hooks,H., Angewandte Chemie, 1966, vol. 78, p. 681
  作者：Ottmann,G.、Hooks,H.

  DOI：——

  日期：——
• Chlorination of Isothiocyanates. II. N-Aryl- and N-Alkyl-S-chloroisothiocarbamoyl Chlorides, a Novel Class of Sulfenyl Chlorides
  作者：Gerhard Ottmann、Haywood Hooks

  DOI：10.1021/jo01341a046

  日期：1966.3
• 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.