3-氯-4-戊氧基-1,2,5-噻二唑 | 178368-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氯-4-戊氧基-1,2,5-噻二唑
• 英文名称: 3-Chloro-4-pentyloxy-1,2,5-thiadiazole
• 英文别名: 1,2,5-Thiadiazole, 3-chloro-4-(pentyloxy)-；3-chloro-4-pentoxy-1,2,5-thiadiazole
• CAS: 178368-38-2
• 化学式: C₇H₁₁ClN₂OS
• 分子量: 206.696
• InChiKey: LCIXELKKGRTCSN-UHFFFAOYSA-N

物化性质

• 沸点：
  253.7±20.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯-4-戊氧基-1,2,5-噻二唑 、 奎宁环-3-醇 在 potassium tert-butylate 作用下， 生成 3-(4-Pentyloxy-[1,2,5]thiadiazol-3-yloxy)-1-aza-bicyclo[2.2.2]octane
  参考文献：
  名称：

  1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists

  摘要：

  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.

  DOI：

  10.1021/jm970125n
• 作为产物：
  描述：

  2-Nitrilo-acetimidic acid pentyl ester 在 sulfur monochloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-氯-4-戊氧基-1,2,5-噻二唑
  参考文献：
  名称：

  1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists

  摘要：

  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.

  DOI：

  10.1021/jm970125n

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。
• 3,4-Dioxy-1,2,5-thiadiazoles partly useful as fungicides
  申请人：Tosoh Corporation

  公开号：EP0621272B1

  公开（公告）日：1997-11-19
• US5478849A
  申请人：——

  公开号：US5478849A

  公开（公告）日：1995-12-26