7-(acetonyloxy)-5-methoxy-4-methylcoumarin | 161837-59-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(acetonyloxy)-5-methoxy-4-methylcoumarin
• 英文别名: 5-Methoxy-4-methyl-7-(2-oxopropoxy)chromen-2-one
• CAS: 161837-59-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: SIDPXAGVOHXPCV-UHFFFAOYSA-N

物化性质

• 沸点：
  457.3±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(acetonyloxy)-5-methoxy-4-methylcoumarin 在 sodium hydroxide 、 alkaline phosphatase 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  4‘-Methyl Derivatives of 5-MOP and 5-MOA:  Synthesis, Photoreactivity, and Photobiological Activity

  摘要：

  The synthesis and photobiological activity of four new 4'-methyl derivatives of 5-MOP (5-methoxypsoralen) and 5-MOA (5-methoxyangelicin), i.e., 4,4'-dimethyl-5-methoxypsoralen, 3,4'-dimethyl-5-methoxypsoralen, 4,4'-dimethyl-5-methoxyangelicin, and 3,4'-dimethyl-5-methoxyangelicin, are described. All these compounds photobind efficiently to DNA. The DNA-photobinding process was investigated using various nucleic acid structures such as double-helix DNA, bacterial DNA, and synthetic polydeoxyribonucleotides. Photoreaction experiments showed that, unlike 8-MOP (8-methoxypsoralen) and 5-MOP, both angular derivatives bind thymine and cytosine with the same efficiency. The principal nucleoside-psoralen monoadducts were isolated and characterized after enzymatic digestion or acid hydrolysis. Biological activity studies revealed a good correlation with the extent of covalent photoaddition. Moreover, the two angular derivatives and the 4,4'-dimethyl-5-methoxypsoralen were unable to induce skin erythema, in striking contrast with the reference drugs, 8-MOP and 5-MOP; only the 3,4'-dimethyl-5-methoxypsoralen caused erythema, although to a substantially lower extent than that induced by the two parent compounds.

  DOI：

  10.1021/jm960117r
• 作为产物：
  描述：

  夫拉美诺 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 7-(acetonyloxy)-5-methoxy-4-methylcoumarin
  参考文献：
  名称：

  Antonello, Cipriano; Zagotto, Giuseppe; Miranda, Rocio, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 11, p. 651 - 654

  摘要：

  DOI：