7-Hydroxy-10-methyl-1,2,3,4-tetrahydro-[1]benzofuro[6,5-c]isochromen-5-one | 570413-72-8

• 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-Hydroxy-10-methyl-1,2,3,4-tetrahydro-[1]benzofuro[6,5-c]isochromen-5-one
• CAS: 570413-72-8
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: QSNIRJDVNRGSFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 7-Hydroxy-10-methyl-1,2,3,4-tetrahydro-[1]benzofuro[6,5-c]isochromen-5-one 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以62%的产率得到7-[3-(Dimethylamino)propoxy]-10-methyl-1,2,3,4-tetrahydro-[1]benzofuro[6,5-c]isochromen-5-one
  参考文献：
  名称：

  Novel Pyrone Side Tetracyclic Psoralen Derivatives:  Synthesis and Photobiological Evaluation

  摘要：

  This study reports the synthesis of tetrahydrobenzo- (4-6) and benzopsoralen (7-9) derivatives obtained by condensing the fourth ring to the pyrone side of the tricyclic psoralen moiety. The new compounds are characterized by having a methoxy, a hydroxy, or a dimethylaminopropoxy side chain inserted at position 8 of the psoralen chromophore. The evaluation of the photoantiproliferative activity on human tumor cell lines along with skin phototoxicity on guinea pigs revealed an interesting photobiological pattern for the dimethylaminopropoxy derivatives 6 and 9: they are in fact able to exert an antiproliferative effect up to 1 order of magnitude higher than that of the well-known drug 8-MOP, but they are devoid of skin phototoxicity. The ability of both 6 and 9 to photoadd to DNA is demonstrated by the isolation and characterization of the 4',5'-monoadducts. AM1 calculations were also performed to gain further insight into the molecular basis of their photobiological behavior.

  DOI：

  10.1021/jm0210919
• 作为产物：
  描述：

  2-甲氧基间苯二酚 在 sodium hydroxide 、 三氯化铝 、 硫酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 61.0h， 生成 7-Hydroxy-10-methyl-1,2,3,4-tetrahydro-[1]benzofuro[6,5-c]isochromen-5-one
  参考文献：
  名称：

  Novel Pyrone Side Tetracyclic Psoralen Derivatives:  Synthesis and Photobiological Evaluation

  摘要：

  This study reports the synthesis of tetrahydrobenzo- (4-6) and benzopsoralen (7-9) derivatives obtained by condensing the fourth ring to the pyrone side of the tricyclic psoralen moiety. The new compounds are characterized by having a methoxy, a hydroxy, or a dimethylaminopropoxy side chain inserted at position 8 of the psoralen chromophore. The evaluation of the photoantiproliferative activity on human tumor cell lines along with skin phototoxicity on guinea pigs revealed an interesting photobiological pattern for the dimethylaminopropoxy derivatives 6 and 9: they are in fact able to exert an antiproliferative effect up to 1 order of magnitude higher than that of the well-known drug 8-MOP, but they are devoid of skin phototoxicity. The ability of both 6 and 9 to photoadd to DNA is demonstrated by the isolation and characterization of the 4',5'-monoadducts. AM1 calculations were also performed to gain further insight into the molecular basis of their photobiological behavior.

  DOI：

  10.1021/jm0210919

文献信息

• Novel Pyrone Side Tetracyclic Psoralen Derivatives:  Synthesis and Photobiological Evaluation
  作者：Lisa Dalla Via、Eugenio Uriarte、Elias Quezada、Alessandro Dolmella、Maria Grazia Ferlin、Ornella Gia

  DOI：10.1021/jm0210919

  日期：2003.8.1

  This study reports the synthesis of tetrahydrobenzo- (4-6) and benzopsoralen (7-9) derivatives obtained by condensing the fourth ring to the pyrone side of the tricyclic psoralen moiety. The new compounds are characterized by having a methoxy, a hydroxy, or a dimethylaminopropoxy side chain inserted at position 8 of the psoralen chromophore. The evaluation of the photoantiproliferative activity on human tumor cell lines along with skin phototoxicity on guinea pigs revealed an interesting photobiological pattern for the dimethylaminopropoxy derivatives 6 and 9: they are in fact able to exert an antiproliferative effect up to 1 order of magnitude higher than that of the well-known drug 8-MOP, but they are devoid of skin phototoxicity. The ability of both 6 and 9 to photoadd to DNA is demonstrated by the isolation and characterization of the 4',5'-monoadducts. AM1 calculations were also performed to gain further insight into the molecular basis of their photobiological behavior.