3-(2,4-dimethoxyphenyl)-4-hydroxy-1-benzopyran-2-one | 124010-40-8

• 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: 3-(2,4-dimethoxyphenyl)-4-hydroxy-1-benzopyran-2-one
• 英文别名: 3-(2,4-Dimethoxyphenyl)-4-hydroxychromen-2-one
• CAS: 124010-40-8
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: NELDCBYLEDKEFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

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 、 lithium hydroxide 作用下， 以 甲醚 、 水 为溶剂， 反应 14.5h， 生成 3-(2,4-dimethoxyphenyl)-4-hydroxy-1-benzopyran-2-one
  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

• Barton, Derek H. R.; Donnelly, Dervilla M. X.; Finet, Jean-Pierre, Journal of the Chemical Society. Perkin transactions I, 1992, p. 1365 - 1376
  作者：Barton, Derek H. R.、Donnelly, Dervilla M. X.、Finet, Jean-Pierre、Guiry, Patrick J.

  DOI：——

  日期：——
• A facile synthesis of 3-aryl-4-hydroxycoumarins
  作者：Derek H.R. Barton、Dervilla M.X. Donnelly、Jean-Pierre Finet、Patrick J. Guiry

  DOI：10.1016/s0040-4039(00)99513-3

  日期：1989.1
• BARTON, DEREK H. R.;DONNELLY, DERVILLA M. X.;FINET, JEAN-PIERRE;GUIRY, PA+, TETRAHEDRON LETT., 30,(1989) N2, C. 1539-1542
  作者：BARTON, DEREK H. R.、DONNELLY, DERVILLA M. X.、FINET, JEAN-PIERRE、GUIRY, PA+

  DOI：——

  日期：——
• 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.