2-{5-[3-(Trifluoromethyl)phenyl]-2H-1,2,3,4-tetraazol-2-YL}acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{5-[3-(Trifluoromethyl)phenyl]-2H-1,2,3,4-tetraazol-2-YL}acetic acid
• 英文别名: 2-[5-[3-(trifluoromethyl)phenyl]tetrazol-2-yl]acetic acid
• 化学式: C₁₀H₇F₃N₄O₂
• mdl: MFCD00208094
• 分子量: 272.186
• InChiKey: ORQVNLNFZQDZAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-{5-[3-(Trifluoromethyl)phenyl]-2H-1,2,3,4-tetraazol-2-YL}acetic acid 、 1-环己基-3-甲基-1H-吡唑-5-胺 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 以27%的产率得到N-(1-cyclohexyl-3-methyl-1H-pyrazol-5-yl)-2-(5-(3-(trifluoromethyl)phenyl)-2H-tetrazol-2-yl)acetamide
  参考文献：
  名称：

  Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

  摘要：

  The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

  DOI：

  10.1016/j.bmcl.2019.01.027
• 作为产物：
  描述：

  间三氟甲基苯腈 在 sodium azide 、 sodium ethanolate 、 三乙胺盐酸盐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 生成 2-{5-[3-(Trifluoromethyl)phenyl]-2H-1,2,3,4-tetraazol-2-YL}acetic acid
  参考文献：
  名称：

  Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

  摘要：

  The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

  DOI：

  10.1016/j.bmcl.2019.01.027