4-(2-methylsulfanyl-ethyl)-[1,2,5]thiadiazol-3-ol | 6595-75-1

• 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-(2-methylsulfanyl-ethyl)-[1,2,5]thiadiazol-3-ol
• 英文别名: 3-(2-methylthioethyl)-4-hydroxy-1,2,5-thiadiazole；4-(2-Methylsulfanylethyl)-1,2,5-thiadiazol-3-one
• CAS: 6595-75-1
• 化学式: C₅H₈N₂OS₂
• 分子量: 176.263
• InChiKey: CMRHXADPWHDUBA-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-methylsulfanyl-ethyl)-[1,2,5]thiadiazol-3-ol 在 过氧乙酸 、 potassium tert-butylate 作用下， 以 氯仿 为溶剂， 生成 4-vinyl-[1,2,5]thiadiazol-3-one
  参考文献：
  名称：

  The synthesis of symmetrical bis-1,2,5-thiadiazole ligands

  摘要：

  We have been engaged in a search for coordination catalysts for the copolymerization of polar monomers (such as vinyl chloride and vinyl acetate) with ethylene. We have been investigating complexes of late transition metals with heterocyclic ligands. In this report we describe the synthesis of a symmetrical bis-thiadiazole. We have characterized one of the intermediates using single crystal X-ray diffraction. Several unsuccessful approaches toward 1 are also described, which shed light on some of the unique chemistry of thiadiazoles. (C) 2004 lsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.045
• 作为产物：
  描述：

  methioninamide hydrochloride 在 吡啶 、 N-亚磺酰苯胺 作用下， 以 正己烷 为溶剂， 反应 16.0h， 生成 4-(2-methylsulfanyl-ethyl)-[1,2,5]thiadiazol-3-ol
  参考文献：
  名称：

  The synthesis of symmetrical bis-1,2,5-thiadiazole ligands

  摘要：

  We have been engaged in a search for coordination catalysts for the copolymerization of polar monomers (such as vinyl chloride and vinyl acetate) with ethylene. We have been investigating complexes of late transition metals with heterocyclic ligands. In this report we describe the synthesis of a symmetrical bis-thiadiazole. We have characterized one of the intermediates using single crystal X-ray diffraction. Several unsuccessful approaches toward 1 are also described, which shed light on some of the unique chemistry of thiadiazoles. (C) 2004 lsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.045

文献信息

• Heterocyclic compounds and their preparation and use
  申请人：Eli Lilly and Company

  公开号：US05646289A1

  公开（公告）日：1997-07-08

  The present invention relates to therapeutically active azacyclic or azabicyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system caused by malfunctioning of the muscarinic cholinergic system.

  本发明涉及具有治疗活性的氮杂环或氮杂双环化合物，一种制备这些化合物的方法以及包含这些化合物的药物组合物。这些新型化合物在治疗由于肌碱胆碱系统功能失调而引起的中枢神经系统疾病方面具有用途。
• Use of azacyclic or azabicyclic thiadiazole compounds for treating anxiety
  申请人：ELI LILLY AND COMPANY

  公开号：EP0774256A1

  公开（公告）日：1997-05-21

  The present invention provides a method for treating anxiety in humans using azacyclic or azabicyclic thiadiazole compounds.

  本发明提供了一种治疗人类焦虑症的方法，使用氮杂环或氮杂双环噻二唑化合物。
• Method for treating anxiety
  申请人：Eli Lilly and Company

  公开号：US05852037A1

  公开（公告）日：1998-12-22

  The present invention provides a method for treating anxiety in humans using azacyclic or azabicyclic compounds.

  本发明提供了一种治疗人类焦虑症的方法，使用氮杂环或氮杂双环化合物。
• Process for preparing 1,2,5-thiadiazole containing ethers
  申请人：Eli Lilly and Company

  公开号：US06040442A1

  公开（公告）日：2000-03-21

  The presently claimed process provides a method for preparing compounds of the formula ##STR1## phosphorous (III) compound and a diester of azodicarboxylate.

  目前所宣称的方法提供了一种制备化合物的方法的公式为##STR1##磷（III）化合物和双酯基的方法。
• 1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists
  作者：John S. Ward、Leander Merritt、David O. Calligaro、Franklin P. Bymaster、Harlan E. Shannon、Charles H. Mitch、Celia Whitesitt、David Brunsting、Malcolm J. Sheardown、Preben H. Olesen、Michael D. B. Swedberg、Lone Jeppesen、Per Sauerberg

  DOI：10.1021/jm970125n

  日期：1998.1.1

  The acetyl group of the muscarinic agonist aceclidine 4 was replaced by various 1,2,5-thiadiazoles to provide a new series of potent m(1) muscarinic agonists 17 and 18. Optimal mi muscarinic agonist potency was achieved when the 1,2,g-thiadiazole substituent was either a butyloxy, 17d, or butylthio, 18d, group. Although 1,2,5-oxadiazole 37 and pyrazine 39 are iso-pi-electronic with 1,2,5-thiadiazole 17d, both analogues were substantially less active than 17d. Compounds with high muscarinic affinity and/or m(1) muscarinic agonist efficacy were also obtained when the 3-oxyquinuclidine moiety of 17d or 18c was replaced by ethanolamines, hydroxypyrrolidines, hydroxyazetidine, hydroxyisotropanes, or hydroxyazanorbornanes. The structure-activity data support the participation of the oxygen or sulfur atom in the substituent on the 1,2,5-thiadiazole in the activation of the m(1) receptor. Several of these new 1,2,5-thiadiazoles have m(1) agonist efficacy, potency, and selectivity comparable to those of xanomeline 2 in the muscarinic tests investigated.