Dimethyl-thiocarbamic acid O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) ester | 473434-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: Dimethyl-thiocarbamic acid O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) ester
• CAS: 473434-25-2
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: UEVDVWZUCHPJRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.57
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Dimethyl-thiocarbamic acid O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.03h， 生成 7-mercapto-4-methyl-8-azacoumarin
  参考文献：
  名称：

  Synthesis, photobiological activity and photoreactivity of methyl-thieno-8-azacoumarins, novel bioisosters of psoralen

  摘要：

  4,4'-dimethyl-thieno-8-azacoumarin (6) and 4,4',5'-trimethyl-thieno-8-azacoumarin (8) were synthesised. Their photobiological activity was tested on human tumour cell lines. Interestingly, for 6, a photocytotoxic ability higher in HL-60, comparable in HeLa cells, with respect to that of the well-known drug 8-methoxypsoralen (8-MOP), was demonstrated. The covalent photoaddition to DNA occurs by means of the molecular mechanism already demonstrated for furocoumarins. However, it is noteworthy that no skin phototoxicity appears.

  DOI：

  10.1016/s0960-894x(02)00152-x
• 作为产物：
  描述：

  二甲氨基硫代甲酰氯 、 7-hydroxy-4-methylpyrano<2,3-b>pyridin-2-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 Dimethyl-thiocarbamic acid O-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) ester
  参考文献：
  名称：

  Synthesis, photobiological activity and photoreactivity of methyl-thieno-8-azacoumarins, novel bioisosters of psoralen

  摘要：

  4,4'-dimethyl-thieno-8-azacoumarin (6) and 4,4',5'-trimethyl-thieno-8-azacoumarin (8) were synthesised. Their photobiological activity was tested on human tumour cell lines. Interestingly, for 6, a photocytotoxic ability higher in HL-60, comparable in HeLa cells, with respect to that of the well-known drug 8-methoxypsoralen (8-MOP), was demonstrated. The covalent photoaddition to DNA occurs by means of the molecular mechanism already demonstrated for furocoumarins. However, it is noteworthy that no skin phototoxicity appears.

  DOI：

  10.1016/s0960-894x(02)00152-x