11-methoxy-4-methyl-2H-benzofuro[3,2-g]-1-benzopyran-2-one | 167023-40-7

• 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: 11-methoxy-4-methyl-2H-benzofuro[3,2-g]-1-benzopyran-2-one
• 英文别名: 11-Methoxy-4-methyl-[1]benzofuro[3,2-g]chromen-2-one
• CAS: 167023-40-7
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: RZQZKJSZNMFWIH-UHFFFAOYSA-N

物化性质

• 熔点：
  191-193 °C
• 沸点：
  502.6±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-methoxy-4-methyl-2H-benzofuro[3,2-g]-1-benzopyran-2-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85.5%的产率得到11-hydroxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
  参考文献：
  名称：

  New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity

  摘要：

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.

  DOI：

  10.1021/jm9910829
• 作为产物：
  描述：

  2-氯环己酮 在 sodium hydroxide 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 59.0h， 生成 11-methoxy-4-methyl-2H-benzofuro[3,2-g]-1-benzopyran-2-one
  参考文献：
  名称：

  New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity

  摘要：

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.

  DOI：

  10.1021/jm9910829

文献信息

• New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity
  作者：Lisa Dalla Via、Ornella Gia、Sebastiano Marciani Magno、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1021/jm9910829

  日期：1999.10.1

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.