4-allyl-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazole-3-thiol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-allyl-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazole-3-thiol
• 英文别名: 3-[(4,6-Dimethylpyrimidin-2-ylthio)methyl]-4-prop-2-enyl-1,2,4-triazoline-5-th ione；3-[(4,6-dimethylpyrimidin-2-yl)sulfanylmethyl]-4-prop-2-enyl-1H-1,2,4-triazole-5-thione
• 化学式: C₁₂H₁₅N₅S₂
• 分子量: 293.417
• InChiKey: PKUUPFYSSZCCEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-N-(3,4-二甲基苯基)乙酰胺 、 4-allyl-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazole-3-thiol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21%的产率得到2-[4-allyl-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(3,4-dimethylphenyl)acetamide
  参考文献：
  名称：

  Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2–S100A10 protein interaction

  摘要：

  Recent target validation studies have shown that inhibition of the protein interaction between annexin A2 and the S100A10 protein may have potential therapeutic benefits in cancer. Virtual screening identified certain 3,4,5-trisubstituted 4H-1,2,4-triazoles as moderately potent inhibitors of this interaction. A series of analogues were synthesized based on the 1,2,4-triazole scaffold and were evaluated for inhibition of the annexin A2-S100A10 protein interaction in competitive binding assays. 2-[(5-{[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]methyl}-4-(furan-2-ylmethyl)-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[4-(propan-2-yl)phenyl]acetamide (36) showed improved potency and was shown to disrupt the native complex between annexin A2 and S100A10.

  DOI：

  10.1016/j.bmc.2014.07.043
• 作为产物：
  描述：

  4,6-二甲基-2-巯基嘧啶 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 4-allyl-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazole-3-thiol
  参考文献：
  名称：

  Design, synthesis and SAR exploration of tri-substituted 1,2,4-triazoles as inhibitors of the annexin A2–S100A10 protein interaction

  摘要：

  Recent target validation studies have shown that inhibition of the protein interaction between annexin A2 and the S100A10 protein may have potential therapeutic benefits in cancer. Virtual screening identified certain 3,4,5-trisubstituted 4H-1,2,4-triazoles as moderately potent inhibitors of this interaction. A series of analogues were synthesized based on the 1,2,4-triazole scaffold and were evaluated for inhibition of the annexin A2-S100A10 protein interaction in competitive binding assays. 2-[(5-{[(4,6-Dimethylpyrimidin-2-yl)sulfanyl]methyl}-4-(furan-2-ylmethyl)-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[4-(propan-2-yl)phenyl]acetamide (36) showed improved potency and was shown to disrupt the native complex between annexin A2 and S100A10.

  DOI：

  10.1016/j.bmc.2014.07.043