1,6-bis[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-ylthio]hexane | 390799-95-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,6-bis[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-ylthio]hexane
• 英文别名: 3-Pyridin-3-yl-4-[6-[(4-pyridin-3-yl-1,2,5-thiadiazol-3-yl)sulfanyl]hexylsulfanyl]-1,2,5-thiadiazole
• CAS: 390799-95-8
• 化学式: C₂₀H₂₀N₆S₄
• 分子量: 472.683
• InChiKey: ZQHMFBDWXIBLON-UHFFFAOYSA-N

物化性质

• 熔点：
  62-62.5 °C
• 沸点：
  656.7±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  184
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,6-bis[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-ylthio]hexane 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 38.0h， 生成 1,6-Di[4-(1-methyl-1,2,3,6-tetrahydro-5-pyridinyl)-1,2,5-thiadiazol-3-ylsulfanyl]hexane
  参考文献：
  名称：

  Design, Synthesis, and Biological Characterization of Bivalent 1-Methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole Derivatives as Selective Muscarinic Agonists

  摘要：

  Selective muscarinic agonists could be useful in the treatment of neurological disorders such as Alzheimer's disease, schizophrenia, and chronic pain. Many muscarinic agonists have been developed, yet most exhibit at best limited functional selectivity for a given receptor subtype perhaps because of the high degree of sequence homology within the putative binding site, which appears to be buried within the transmembrane domains. Bivalent compounds containing essentially two agonist pharmacophores within the same molecule were synthesized and tested for receptor binding affinity and muscarinic agonist activity. A series of bis-1,2,5-thiadiazole derivatives of 1,2,5,6-tetrahydropyridine linked by an alkyloxy moiety exhibited very high affinity (K-i < 1 nM) and strong agonist activity. The degree of activity depended on the length of the linking alkyl group, which could be replaced by a poly(ethylene glycol) moiety, resulting in improved water solubility, binding affinity, and agonist potency.

  DOI：

  10.1021/jm0102405
• 作为产物：
  描述：

  1,6-二溴己烷 、 3-氯-4-(吡啶-3-基)-1,2,5-噻二唑 在 sodium hydrogensulfide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76.2%的产率得到1,6-bis[3-(pyrid-3-yl)-1,2,5-thiadiazol-4-ylthio]hexane
  参考文献：
  名称：

  Design, Synthesis, and Biological Characterization of Bivalent 1-Methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole Derivatives as Selective Muscarinic Agonists

  摘要：

  Selective muscarinic agonists could be useful in the treatment of neurological disorders such as Alzheimer's disease, schizophrenia, and chronic pain. Many muscarinic agonists have been developed, yet most exhibit at best limited functional selectivity for a given receptor subtype perhaps because of the high degree of sequence homology within the putative binding site, which appears to be buried within the transmembrane domains. Bivalent compounds containing essentially two agonist pharmacophores within the same molecule were synthesized and tested for receptor binding affinity and muscarinic agonist activity. A series of bis-1,2,5-thiadiazole derivatives of 1,2,5,6-tetrahydropyridine linked by an alkyloxy moiety exhibited very high affinity (K-i < 1 nM) and strong agonist activity. The degree of activity depended on the length of the linking alkyl group, which could be replaced by a poly(ethylene glycol) moiety, resulting in improved water solubility, binding affinity, and agonist potency.

  DOI：

  10.1021/jm0102405