1-[3-(Methylthio)phenyl]-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazole | 165806-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[3-(Methylthio)phenyl]-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazole
• 英文别名: 1-[3-(methylthio)phenyl]-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole；4-[5-(4-Fluorophenyl)-3-(3-methylsulfanylphenyl)imidazol-4-yl]pyridine
• CAS: 165806-27-9
• 化学式: C₂₁H₁₆FN₃S
• 分子量: 361.443
• InChiKey: KCRPPQYLFPCZML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[3-(Methylthio)phenyl]-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazole 在 dipotassium peroxodisulfate 作用下， 以67%的产率得到1-[3-(Methylsulfinyl)phenyl]-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazole
  参考文献：
  名称：

  Formamide intermediates for the preparation of tri-substituted imidazole compounds with multiple therapeutic properties

  摘要：

  这项发明涉及一类新型的甲酰胺化合物及其制备方法，可用于制备具有多种治疗性能的三取代咪唑。

  公开号：

  EP1227091A3
• 作为产物：
  描述：

  3-氨基茴香硫醚 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 magnesium sulfate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 1-[3-(Methylthio)phenyl]-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazole
  参考文献：
  名称：

  1-Substituted 4-Aryl-5-pyridinylimidazoles:  A New Class of Cytokine Suppressive Drugs with Low 5-Lipoxygenase and Cyclooxygenase Inhibitory Potency

  摘要：

  A series of 1-alkyl- or -aryl-4-aryl-5-pyridinylimidazoles (A) were prepared and tested for their ability to bind to a recently discovered protein kinase termed CSBP and to inhibit lipopolysaccharide (LPS)-stimulated TNF production in mice. The kinase, CSBP, appears to be involved in a signaling cascade initiated by a number of inflammatory stimuli and leading to the biosynthesis of the inflammatory cytokines IL-1 and TNF. Two related imidazole classes (B and C) had previously been reported to bind to CSBP and to inhibit LPS-stimulated human monocyte IL-1 and TNF production. The members of the earlier series exhibited varying degrees of potency as inhibitors of the enzymes of arachidonic acid metabolism, PGHS-1 and 5-LO. Several of the more potent CSBP ligands and TNF biosynthesis inhibitors among the present series of N-1-alkylated imidazoles (A) were tested as inhibitors of PGHS-1 and 5-LO and were found to be weak to inactive as inhibitors of these enzymes. One of the compounds, 9 (SE 210313) which lacked measureable activity as an inhibitor of the enzymes of arachidonate metabolism, and had good potency in the binding and in vivo TNF inhibition assays, was tested for antiarthritic activity in the AA rat model of arthritis. Compound 9 significantly reduced edema and increased bone mineral density in this model.

  DOI：

  10.1021/jm960415o

文献信息

• Formamide intermediates for the preparation of tri-substituted imidazole compounds with multiple therapeutic properties
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1227091A3

  公开（公告）日：2002-08-07

  The invention relates to a novel group of formamide compounds and a process for their preparation, useful in the preparation of tri-substituted imadazoles having multiple therapeutic properties.

  这项发明涉及一类新型的甲酰胺化合物及其制备方法，可用于制备具有多种治疗性能的三取代咪唑。
• Imine intermediates for the preparation of trisubstituted imidazole compounds with multiple therapeutic properties
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1229035A1

  公开（公告）日：2002-08-07

  The invention relates to a novel group of iminc compounds and a process for their preparation, useful in the preparation of tri-substituted imadazoles having multiple therapeutic properties.

  这项发明涉及一类新型的iminc化合物及其制备方法，可用于制备具有多种治疗性能的三取代咪唑。
• Isonitrile intermediates for the preparation of tri-substituted imidazole compounds with multiple therapeutic properties
  申请人：SmithKline Beecham Corporation

  公开号：EP1227092A3

  公开（公告）日：2002-08-07

  The invention relates to a novel group of isonitrile compounds and a process for their preparation, useful in the preparation of tri-substituted imadazoles having multiple therapeutic properties.

  这项发明涉及一类新型异腈化合物及其制备方法，可用于制备具有多种治疗性能的三取代咪唑。
• Novel compounds
  申请人：SmithKline Beecham Corporation

  公开号：US20020188122A1

  公开（公告）日：2002-12-12

  Novel 1, 4, 5- substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  小说1、4、5-取代咪唑化合物和组合物，用于作为细胞因子抑制剂的治疗。
• Process for the preparation of trisubstituted imidazole compounds with multiple therapeutic properties
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1291346A1

  公开（公告）日：2003-03-12

  Novel 1,4,5- substituted imidazole compounds and compositions for use in therapy.

  用于治疗的新型 1,4,5-取代咪唑化合物和组合物。