4-(benzyloxy)-3-phenylcoumarin | 1399134-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-(benzyloxy)-3-phenylcoumarin
• 英文别名: 3-Phenyl-4-phenylmethoxychromen-2-one
• CAS: 1399134-34-9
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: NIXBUQWTLKSDLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 三叔丁基膦 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 lithium hydroxide 作用下， 以 甲醚 、 水 、 丙酮 为溶剂， 反应 26.5h， 生成 4-(benzyloxy)-3-phenylcoumarin
  参考文献：
  名称：

  Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives

  摘要：

  Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7-dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 mu M) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.099

文献信息

• Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives
  作者：Silvia Serra、Andrea Chicca、Giovanna Delogu、Saleta Vázquez-Rodríguez、Lourdes Santana、Eugenio Uriarte、Laura Casu、Jürg Gertsch

  DOI：10.1016/j.bmcl.2012.07.099

  日期：2012.9

  Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7-dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 mu M) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies. (c) 2012 Elsevier Ltd. All rights reserved.