5-(4-fluorophenyl)-4-pyridin-3-yl-1H-pyrimidine-2-thione | 444719-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(4-fluorophenyl)-4-pyridin-3-yl-1H-pyrimidine-2-thione
• 英文别名: 5-(4-fluorophenyl)-6-pyridin-3-yl-1H-pyrimidine-2-thione
• CAS: 444719-88-4
• 化学式: C₁₅H₁₀FN₃S
• 分子量: 283.329
• InChiKey: ODEPTYOJZWHHNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(甲基硫代)苄氯 、 5-(4-fluorophenyl)-4-pyridin-3-yl-1H-pyrimidine-2-thione 在 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以45%的产率得到5-(4-fluorophenyl)-2-(4-methylsulfanylbenzylsulfanyl)-4-pyridin-3-ylpyrimidine
  参考文献：
  名称：

  From Imidazoles to Pyrimidines:  New Inhibitors of Cytokine Release

  摘要：

  On the basis of model imidazole inhibitors of cytokine release, a series of novel pyridinyl pyrimidine derivatives was prepared and tested on their ability to inhibit the release of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) and human whole blood. In the pyrimidine series, structure-activity relationships (SARs) similar to those of the imidazole series were found, although generally pyrimidine compounds were less potent. Modification of the substituent at the 2 position of the pyrimidine led to the most active compound 14 which inhibited release of TNF-alpha (IC50 = 3.2 muM) and IL-1beta (IC50 = 2.3 muM) from PBMC as effectively as the model imidazole inhibitor ML 3163 (TNF-alpha, IC50 = 3.7 muM; IL-1beta, IC50 = 0-9 muM). Screening in an isolated enzyme assay revealed both imidazole and pyrimidine compounds as inhibitors of p38 MAP (mitogen-activated protein) kinase.

  DOI：

  10.1021/jm011098a
• 作为产物：
  描述：

  2-(4-氟苯基)-1-(3-吡啶基)-乙酮 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.5h， 生成 5-(4-fluorophenyl)-4-pyridin-3-yl-1H-pyrimidine-2-thione
  参考文献：
  名称：

  From Imidazoles to Pyrimidines:  New Inhibitors of Cytokine Release

  摘要：

  On the basis of model imidazole inhibitors of cytokine release, a series of novel pyridinyl pyrimidine derivatives was prepared and tested on their ability to inhibit the release of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) and human whole blood. In the pyrimidine series, structure-activity relationships (SARs) similar to those of the imidazole series were found, although generally pyrimidine compounds were less potent. Modification of the substituent at the 2 position of the pyrimidine led to the most active compound 14 which inhibited release of TNF-alpha (IC50 = 3.2 muM) and IL-1beta (IC50 = 2.3 muM) from PBMC as effectively as the model imidazole inhibitor ML 3163 (TNF-alpha, IC50 = 3.7 muM; IL-1beta, IC50 = 0-9 muM). Screening in an isolated enzyme assay revealed both imidazole and pyrimidine compounds as inhibitors of p38 MAP (mitogen-activated protein) kinase.

  DOI：

  10.1021/jm011098a

文献信息

• From Imidazoles to Pyrimidines:  New Inhibitors of Cytokine Release
  作者：Stefan A. Laufer、Gerd K. Wagner

  DOI：10.1021/jm011098a

  日期：2002.6.1

  On the basis of model imidazole inhibitors of cytokine release, a series of novel pyridinyl pyrimidine derivatives was prepared and tested on their ability to inhibit the release of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) and human whole blood. In the pyrimidine series, structure-activity relationships (SARs) similar to those of the imidazole series were found, although generally pyrimidine compounds were less potent. Modification of the substituent at the 2 position of the pyrimidine led to the most active compound 14 which inhibited release of TNF-alpha (IC50 = 3.2 muM) and IL-1beta (IC50 = 2.3 muM) from PBMC as effectively as the model imidazole inhibitor ML 3163 (TNF-alpha, IC50 = 3.7 muM; IL-1beta, IC50 = 0-9 muM). Screening in an isolated enzyme assay revealed both imidazole and pyrimidine compounds as inhibitors of p38 MAP (mitogen-activated protein) kinase.