4-[5-(4-fluorophenyl)-2-phenethylsulfanyl-1H-imidazol-4-yl]-pyridine | 475585-61-6

• 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-[5-(4-fluorophenyl)-2-phenethylsulfanyl-1H-imidazol-4-yl]-pyridine
• 英文别名: 4-[4-(4-fluorophenyl)-2-(2-phenylethylsulfanyl)-1H-imidazol-5-yl]pyridine
• CAS: 475585-61-6
• 化学式: C₂₂H₁₈FN₃S
• 分子量: 375.469
• InChiKey: OZERNEWZWUTUIC-UHFFFAOYSA-N

物化性质

• 熔点：
  257 °C
• 沸点：
  561.4±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氯乙苯 、 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydro-imidazole-2-thione 在 sodium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 70.0h， 以42%的产率得到4-[5-(4-fluorophenyl)-2-phenethylsulfanyl-1H-imidazol-4-yl]-pyridine
  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

文献信息

• 2-Thio-substituted imidazole derivatives and their use in pharmaceutics
  申请人：Laufer Stefan

  公开号：US20060235054A1

  公开（公告）日：2006-10-19

  The invention relates to 2-thio-substituted imidazole derivatives of the formula I in which the radicals R 1 , R 2 R 3 and m are as defined in the description. The compounds according to the invention have immunomodulating and/or cytokine-release-inhibiting action and are therefore suitable for treating disorders associated with a disturbed immune system.

  本发明涉及公式I中的2-硫代取代咪唑衍生物，其中基团R1，R2，R3和m如描述中所定义。本发明的化合物具有免疫调节和/或细胞因子释放抑制作用，因此适用于治疗与免疫系统紊乱相关的疾病。
• US7582660B2
  申请人：——

  公开号：US7582660B2

  公开（公告）日：2009-09-01