3-(4-(4-fluorophenyl)-1-methyl-5-(pyridin-4-yl)-1H-imidazol-2-ylthio)propane-1,2-diol | 627080-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-(4-fluorophenyl)-1-methyl-5-(pyridin-4-yl)-1H-imidazol-2-ylthio)propane-1,2-diol
• 英文别名: 3-(4-(4-Fluorophenyl)-1-methyl-5-(pyridin-4yl)-1H-imidazol-2-ylthio)propane-1,2-diol；3-[4-(4-fluorophenyl)-1-methyl-5-pyridin-4-ylimidazol-2-yl]sulfanylpropane-1,2-diol
• CAS: 627080-91-5
• 化学式: C₁₈H₁₈FN₃O₂S
• 分子量: 359.424
• InChiKey: QMSCAASWXAIQKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴-1,2-并二酚 、 4-(4-fluorophenyl)-1-methyl-5-(pyridin-4-yl)-1H-imidazole-2-thione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以43%的产率得到3-(4-(4-fluorophenyl)-1-methyl-5-(pyridin-4-yl)-1H-imidazol-2-ylthio)propane-1,2-diol
  参考文献：
  名称：

  Targeting the Ribose and Phosphate Binding Site of p38 Mitogen-Activated Protein (MAP) Kinase: Synthesis and Biological Testing of 2-Alkylsulfanyl-, 4(5)-Aryl-, 5(4)-Heteroaryl-Substituted Imidazoles

  摘要：

  Three series of substituted 2-alkylsulfanyl-4-(4-fluorophenyl)imidazoles, 5-pyridinyl-, 1-methyl-5-pyridinyl-, and 5-(2-aminopyridin-4-yl)-imidazoles, were prepared and tested for their ability to inhibit p38 MAP kinase and TNF-alpha release. These compounds were prepared by using different synthetic routes. They were tested by applying a nonradioactive p38 MAP kinase assay and by measurement of TNF-a release in human whole blood. Potent inhibitors (IC(50)values in the low nanomolar range, as low as 2 nM in the enzyme assay and 37 nM in the human whole blood test) were identified by variation of substituents at the imidazole-C2-thio position as well as at the 2-aminopyridinyl functionality. In contrast to other known kinase inhibitors, these novel imidazole derivatives with the substituents at the imidazole-C2-thio position may interact with the ribose as well as with the phosphate binding site of the p38 MAP kinase.

  DOI：

  10.1021/jm800373t

文献信息

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

  公开号：US20060252810A1

  公开（公告）日：2006-11-09

  The invention relates to 2-thio-substituted imidazole derivatives of the formula I in which the radicals R 1 , R 2 , R 3 , R 4 and p 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，R4和p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有关的疾病。
• US7442713B2
  申请人：——

  公开号：US7442713B2

  公开（公告）日：2008-10-28