7-acetonyloxy-3,4-cyclohexene-8-methoxycoumarin | 570413-70-6

• 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-3,4-cyclohexene-8-methoxycoumarin
• 英文别名: 4-methoxy-3-(2-oxopropoxy)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one；4-methoxy-3-(2-oxopropoxy)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
• CAS: 570413-70-6
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: LJECJUBXWWXOGP-UHFFFAOYSA-N

物化性质

• 沸点：
  501.6±50.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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-3,4-cyclohexene-8-methoxycoumarin 在 sodium hydroxide 、 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 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
• 作为产物：
  描述：

  2-甲氧基间苯二酚 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 34.0h， 生成 7-acetonyloxy-3,4-cyclohexene-8-methoxycoumarin
  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

• Quantitative Structure−Activity Relationship and Complex Network Approach to Monoamine Oxidase A and B Inhibitors
  作者：Lourdes Santana、Humberto González-Díaz、Elías Quezada、Eugenio Uriarte、Matilde Yáñez、Dolores Viña、Francisco Orallo

  DOI：10.1021/jm800656v

  日期：2008.11.13

  The work provides a new model for the prediction of the MAO-A and -B inhibitor activity by the use of combined complex networks and QSAR methodologies. On the basis of the obtained model, we prepared and assayed 33 coumarin derivatives, and the theoretical prediction was compared with the experimental activity data. The model correctly predicted 27 compounds, and most of the active derivatives showed

  这项工作通过使用复杂的网络和QSAR方法，为预测MAO-A和-B抑制剂的活性提供了一个新模型。在获得的模型的基础上，我们制备并测定了33种香豆素衍生物，并将理论预测值与实验活性数据进行了比较。该模型可以正确预测27种化合物，并且大多数活性衍生物对MAO-A和MAO-B同种型的IC 50值均在muM-nM范围内。化合物14显示出与用作参照抑制剂的盐酸高粱碱相同的MAO-A抑制活性（IC 50 = 7.2 nM），并且具有最高的MAO-A特异性（比MAO-B高1000倍）。另一方面，化合物24（IC 50 = 1.2 nM）和28（IC 50 = 1.5 nM）的活性高于司来吉兰（IC 50 = 19）。