4-amino-1-[(2-phenylthiazol-4-yl)methyl]-4H-1,2,4-triazolium chloride | 1346418-30-1

• 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-amino-1-[(2-phenylthiazol-4-yl)methyl]-4H-1,2,4-triazolium chloride
• 英文别名: 1-[(2-Phenyl-1,3-thiazol-4-yl)methyl]-1,2,4-triazol-4-ium-4-amine;chloride
• CAS: 1346418-30-1
• 化学式: C₁₂H₁₂N₅S*Cl
• 分子量: 293.78
• InChiKey: IKRUPNIBPLMXGX-UHFFFAOYSA-M

物化性质

• 熔点：
  173-175 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(2-phenylthiazol-4-yl)methyl]-4H-1,2,4-triazolium chloride 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以97%的产率得到1-[(2-phenylthiazol-4-yl)methyl]-1H-1,2,4-triazole
  参考文献：
  名称：

  1-[(2-Arylthiazol-4-yl)methyl]azoles as a New Class of Anticonvulsants: Design, Synthesis, In vivo Screening, and In silico Drug-like Properties

  摘要：

  A series of novel thiazole incorporated (arylalkyl)azoles were synthesized and screened for their anticonvulsant properties using maximal electroshock and pentylenetetrazole models in mice. Among target compounds, 1‐[(2‐(4‐chlorophenyl)thiazol‐4‐yl)methyl]‐1H‐imidazole (compound 4b), 1‐[(2‐phenylthiazol‐4‐yl)methyl]‐1H‐1,2,4‐tria‐zole (8a), and its 4‐chlorophenyl analog (compound 8b) were able to display noticeable anticonvulsant activity in both pentylenetetrazole and maximal electroshock tests with percentage protection range of 33–100%. A computational study was carried out for prediction of pharmacokinetics properties and drug‐likeness. The structure‐activity relationship and in silico drug relevant properties (molecular weight, topological polar surface area, clog P, hydrogen bond donors, hydrogen bond acceptors, and log BB) confirmed that the compounds were within the range set by Lipinski’s rule‐of‐five, and possessing favorable physicochemical properties for acting as CNS‐drugs, making them potentially promising agents for epilepsy therapy.

  DOI：

  10.1111/j.1747-0285.2011.01211.x
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 、 4-(氯甲基)-2-苯基-1,3-噻唑 以 异丙醇 为溶剂， 反应 36.0h， 以65%的产率得到4-amino-1-[(2-phenylthiazol-4-yl)methyl]-4H-1,2,4-triazolium chloride
  参考文献：
  名称：

  1-[(2-Arylthiazol-4-yl)methyl]azoles as a New Class of Anticonvulsants: Design, Synthesis, In vivo Screening, and In silico Drug-like Properties

  摘要：

  A series of novel thiazole incorporated (arylalkyl)azoles were synthesized and screened for their anticonvulsant properties using maximal electroshock and pentylenetetrazole models in mice. Among target compounds, 1‐[(2‐(4‐chlorophenyl)thiazol‐4‐yl)methyl]‐1H‐imidazole (compound 4b), 1‐[(2‐phenylthiazol‐4‐yl)methyl]‐1H‐1,2,4‐tria‐zole (8a), and its 4‐chlorophenyl analog (compound 8b) were able to display noticeable anticonvulsant activity in both pentylenetetrazole and maximal electroshock tests with percentage protection range of 33–100%. A computational study was carried out for prediction of pharmacokinetics properties and drug‐likeness. The structure‐activity relationship and in silico drug relevant properties (molecular weight, topological polar surface area, clog P, hydrogen bond donors, hydrogen bond acceptors, and log BB) confirmed that the compounds were within the range set by Lipinski’s rule‐of‐five, and possessing favorable physicochemical properties for acting as CNS‐drugs, making them potentially promising agents for epilepsy therapy.

  DOI：

  10.1111/j.1747-0285.2011.01211.x