4-(4-azatricyclo<2.2.1.0^2,6>hept-1-yl)-1,2,5-thiadiazole-3-thiol | 198143-55-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-azatricyclo<2.2.1.0^2,6>hept-1-yl)-1,2,5-thiadiazole-3-thiol
• 英文别名: 4-(4-Azatricyclo[2.2.1.02,6]hept-1-yl)-1,2,5-thiadiazole-3-thiol；4-(4-Azatricyclo[2.2.1.02.6]hept-1-yl)-1,2,5-thiadiazole-3-thiol；4-(4-azatricyclo[2.2.1.02,6]heptan-1-yl)-1,2,5-thiadiazole-3-thione
• CAS: 198143-55-4
• 化学式: C₈H₉N₃S₂
• 分子量: 211.312
• InChiKey: WCHZLVKTZWTMBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-chloro-5-fluorophenyl)prop-2-yn-1-ol 、 4-(4-azatricyclo<2.2.1.0^2,6>hept-1-yl)-1,2,5-thiadiazole-3-thiol 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-(4-Azatricyclo[2.2.1.02,6]heptan-1-yl)-4-[3-(3-chloro-5-fluorophenyl)prop-2-ynylsulfanyl]-1,2,5-thiadiazole
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019
• 作为产物：
  描述：

  2-amino-2-(4-azatricyclo<2,2,1,0^2,6>hept-1-yl)acetonitrile 在 sodium hydrogensulfide 、 sulfur monochloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-(4-azatricyclo<2.2.1.0^2,6>hept-1-yl)-1,2,5-thiadiazole-3-thiol
  参考文献：
  名称：

  1-(1,2,5-Thiadiazol-4-yl)-4-azatricyclo[2.2.1.0^2,6]heptanes as New Potent Muscarinic M₁ Agonists:  Structure−Activity Relationship for 3-Aryl-2-propyn-1-yloxy and 3-Aryl-2-propyn-1-ylthio Derivatives

  摘要：

  Two new series of 1-(1,2,5-thiadiazol-4-yl)-4-azatricyclo[2.2.1.0(2,6)]heptanes were synthesized and evaluated for their in vitro activity in cell lines transfected with either the human M-1 or M-2 receptor. 3-Phenyl-2-propyn-1-yloxy and -1-ylthio analogues substituted with halogen in the meta position showed high functional potency, efficacy, and selectivity toward the M-1 receptor subtype. A quite unique functional M-1 receptor selectivity was observed for compounds 8b, 8d, 8f, 9b, 9d, and 9f. Bioavailability studies in rats indicated an oral bioavailability of about 20-30%, with the N-oxide as the only detected metabolite.

  DOI：

  10.1021/jm9910019

文献信息

• Heterocyclic compounds and their preparation and use
  申请人：Novo Nordisk

  公开号：US05914338A1

  公开（公告）日：1999-06-22

  The present invention relates to therapeutically active azatricyclic compounds of formula I ##STR1## a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating a disease in the central nervous system caused by malfunctioning of the muscarinic cholinergic system.

  本发明涉及公式I的治疗活性氮杂环化合物，其制备方法以及包含该化合物的制药组合物。这些新型化合物可用于治疗由胆碱能肌肉型受体系统功能失调引起的中枢神经系统疾病。
• HETEROCYCLIC COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0891363B1

  公开（公告）日：2003-08-27