8,9,10,11-tetrahydro-5-(3-chloropropoxy)-4-methylbenzofuro[2,3-h]coumarin | 1380207-68-0

• 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: 8,9,10,11-tetrahydro-5-(3-chloropropoxy)-4-methylbenzofuro[2,3-h]coumarin
• CAS: 1380207-68-0
• 化学式: C₁₉H₁₉ClO₄
• 分子量: 346.81
• InChiKey: YTYKTRYYMKAIJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8,9,10,11-tetrahydro-5-(3-chloropropoxy)-4-methylbenzofuro[2,3-h]coumarin 、 盐酸二甲胺 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 以70%的产率得到8,9,10,11-tetrahydro-5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h]coumarin
  参考文献：
  名称：

  A novel tetrahydrobenzoangelicin with dark and photo biological activity

  摘要：

  The synthesis of 8,9,10,11-tetrahydro-5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h] coumarin (5) is described. The new compound showed the ability to inhibit cell growth both upon UVA irradiation and in the dark. The investigation on the mechanism of action highlighted the capacity of 5 to covalently photoadd to thymine, as demonstrated by the isolation and characterization of the 4',5'-monoadduct. Furthermore, in the ground state 5 interferes with the topoisomerase II relaxation activity, suggesting that this enzyme could constitute a molecular target responsible for the dark antiproliferative effect. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.071
• 作为产物：
  描述：

  5-methoxy-4-methyl-7-(2-oxocyclohexyloxy)-2H-chromen-2-one 在 aluminum (III) chloride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 57.25h， 生成 8,9,10,11-tetrahydro-5-(3-chloropropoxy)-4-methylbenzofuro[2,3-h]coumarin
  参考文献：
  名称：

  A novel tetrahydrobenzoangelicin with dark and photo biological activity

  摘要：

  The synthesis of 8,9,10,11-tetrahydro-5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h] coumarin (5) is described. The new compound showed the ability to inhibit cell growth both upon UVA irradiation and in the dark. The investigation on the mechanism of action highlighted the capacity of 5 to covalently photoadd to thymine, as demonstrated by the isolation and characterization of the 4',5'-monoadduct. Furthermore, in the ground state 5 interferes with the topoisomerase II relaxation activity, suggesting that this enzyme could constitute a molecular target responsible for the dark antiproliferative effect. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.071