5-mercapto-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole | 51856-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-mercapto-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole
• 英文别名: 1-methyl-3-trifluoromethyl-1H-1,2,4-triazole-5-thiol；2-methyl-5-(trifluoromethyl)-1H-1,2,4-triazole-3-thione
• CAS: 51856-18-9
• 化学式: C₄H₄F₃N₃S
• 分子量: 183.157
• InChiKey: YQBLDOAHAIFNTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-mercapto-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以89%的产率得到1-methyl-5-methylthio-3-trifluoromethyl-1H-1,2,4-triazole
  参考文献：
  名称：

  WO2006/99957

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基氨基硫脲 、 三氟乙酸 以 甲苯 为溶剂， 以34%的产率得到5-mercapto-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole
  参考文献：
  名称：

  Renin inhibitors containing C-termini derived from mercaptoheterocycles

  摘要：

  A series of transition-state analogues having heterocyclylthio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. Oxidation of the thioether to sulfone was also investigated. Several of the compounds, especially those derived from N1-substituted-5-mercaptotetrazoles or N4-substituted-3-mercapto-5-(trifluoromethyl)-1,2,4-triazoles, were moderately potent inhibitors of human plasma renin, having IC50 values of 30-40 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys at 0.3-1.2 mg/kg, they reduced plasma renin activity by 75-98%. However, this inhibition and the accompanying drop in blood pressure were of short duration.

  DOI：

  10.1021/jm00089a023