[5-(4-氟-苯基)-四唑-2-基]-乙酸 | 436091-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: [5-(4-氟-苯基)-四唑-2-基]-乙酸
• 中文别名: [5-(4-氟苯)-2H-四唑-2-基]乙酸
• 英文名称: [5-(4-Fluoro-phenyl)-tetrazol-2-yl]-acetic acid
• 英文别名: 2-[5-(4-fluorophenyl)tetrazol-2-yl]acetic acid
• CAS: 436091-81-5
• 化学式: C₉H₇FN₄O₂
• mdl: MFCD02623411
• 分子量: 222.179
• InChiKey: BONKJFMYGUGBDH-UHFFFAOYSA-N

物化性质

• 沸点：
  449.8±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  [5-(4-氟-苯基)-四唑-2-基]-乙酸 、 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24%的产率得到N-(1-cyclohexyl-3-methyl-1H-pyrazol-5-yl)-2-(5-(4-fluorophenyl)-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：

  ethyl 5-(4-fluorophenyl)-2H-tetrazol-2-ylacetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [5-(4-氟-苯基)-四唑-2-基]-乙酸
  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

文献信息

• Design and optimization of imidazole derivatives as potent CXCR3 antagonists
  作者：Xiaohui Du、Xiaoqi Chen、Jeffrey T. Mihalic、Jeffrey Deignan、Jason Duquette、An-Rong Li、Bryan Lemon、Ji Ma、Shichang Miao、Karen Ebsworth、Timothy J. Sullivan、George Tonn、Tassie L. Collins、Julio C. Medina

  DOI：10.1016/j.bmcl.2007.11.072

  日期：2008.1

  A series of imidazole derivatives have been designed and optimized for CXCR3 antagonism, pharmacokinetic properties, and reduced formation of glutathione conjugates. Our efforts led to the discovery of potent CXCR3 antagonists with good pharmacokinetic properties. These compounds are useful tools for in vivo studies of CXCR3 function. (c) 2007 Elsevier Ltd. All rights reserved.