8,9,10,11-tetrahydro-5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h]coumarin | 351902-91-5

• 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-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h]coumarin
• 英文别名: 5-[3-(Dimethylamino)propoxy]-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one
• CAS: 351902-91-5
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: KDRKRZSPMBVDSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-Methoxy-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one	161837-63-4	C17H16O4	284.312
  ——	5-methoxy-4-methyl-7-(2-oxocyclohexyloxy)-2H-chromen-2-one	161837-60-1	C17H18O5	302.327
  7-羟基-5-甲氧基-4-甲基-2H-1-苯并吡喃-2-酮	7-hydroxy-5-methoxy-4-methylcoumarin	6093-81-8	C11H10O4	206.198

反应信息

• 作为产物：
  描述：

  2-氯环己酮 在 aluminum (III) chloride 、 potassium carbonate 、 sodium iodide 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 104.25h， 生成 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

文献信息

• A novel tetrahydrobenzoangelicin with dark and photo biological activity
  作者：Lisa Dalla Via、Ornella Gia、Sergio Caffieri、Aída N. García-Argáez、Elías Quezada、Eugenio Uriarte

  DOI：10.1016/j.bmc.2012.03.071

  日期：2012.6

  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.