4-Methyl-7-(1-methyl-2-oxo-propylsulfanyl)-pyrano[2,3-b]pyridin-2-one | 473434-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-Methyl-7-(1-methyl-2-oxo-propylsulfanyl)-pyrano[2,3-b]pyridin-2-one
• CAS: 473434-33-2
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: VGZOWRRROZUMKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.17
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Methyl-7-(1-methyl-2-oxo-propylsulfanyl)-pyrano[2,3-b]pyridin-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 2,3,5-trimethyl-8-oxa-1-thia-9-aza-cyclopenta[b]naphthalen-7-one
  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：

  dimethyl-thiocarbamic acid S-(4-methyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl) ester 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 7.0h， 生成 4-Methyl-7-(1-methyl-2-oxo-propylsulfanyl)-pyrano[2,3-b]pyridin-2-one
  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