[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-ylsulfanyl]-acetonitrile | 220113-44-0

• 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-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-ylsulfanyl]-acetonitrile
• 英文别名: 2-[[4-(4-fluorophenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]sulfanyl]acetonitrile
• CAS: 220113-44-0
• 化学式: C₁₆H₁₁FN₄S
• 分子量: 310.355
• InChiKey: BBJOHWSWEWHYBW-UHFFFAOYSA-N

物化性质

• 熔点：
  219 °C
• 沸点：
  519.1±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氯乙腈 、 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydro-imidazole-2-thione 在 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 以26%的产率得到[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-ylsulfanyl]-acetonitrile
  参考文献：
  名称：

  Imidazole Inhibitors of Cytokine Release:  Probing Substituents in the 2 Position

  摘要：

  Novel 2,4,5-trisubstituted imidazole derivatives were prepared as potential anticytokine agents. Thirty-seven compounds were tested on their ability to inhibit the release of tumor necrosis factor-a (TNF-alpha and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) or human whole blood. SARs (structure activity relationships) for substituents-at the 4 and 5 position of the imidazole core were similar to those described for other inhibitors of cytokine. release and p38 MAP (mitogen-activated protein) kinase. Starting from benzylsulfanyl imidazole 2b (IC50 p(38), 4.0 muM; TNF-alpha, 1.1,muM; IL-1beta, 0.38,muM), the contribution of substituents at the 2 Position to enzyme inhibitory and cellular activity of test compounds was investigated. This strategy led to the identification of compound 2q (IC50 p38, 0.63 muM; TNF-alpha, 0.90 muM; IL-1beta, 0.04,muM), which was 6-10 times more potent than the initial lead 2b with respect to inhibition of p38 and IL-1beta release and equipotently inhibited TNF-alpha release.

  DOI：

  10.1021/jm020873z