7-methoxy-4-[(E)-2-(3-methoxyphenyl)vinyl]-2H-chromen-2-one | 1234330-83-6

• 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-methoxy-4-[(E)-2-(3-methoxyphenyl)vinyl]-2H-chromen-2-one
• 英文别名: 7-methoxy-4-[(E)-2-(3-methoxyphenyl)ethenyl]chromen-2-one
• CAS: 1234330-83-6
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: PMMCZDASBMBABB-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (7-methoxy-2-oxo-2H-chromen-4-ylmethyl)phosphonicacid diethyl ester 、 3-甲氧基苯甲醛 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以54%的产率得到7-methoxy-4-[(E)-2-(3-methoxyphenyl)vinyl]-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents

  摘要：

  The naturally occurring coumarins and resveratrol, attract great attention due to their wide range of biological properties, including anticancer, antileukemic, antibacterial and anti-inflammatory activities; moreover, their cancer chemopreventive property have been recently emphasized. A novel class of hybrid compounds, obtained by introducing a substituted trans-vinylbenzene moiety on a coumarin backbone, was synthesized and evaluated for the antitumor profile. A number of derivatives showed a good antiproliferative activity, in some cases higher to that of the reference compound resveratrol. The most promising compounds in this series were 14 and 17, endowed with excellent antiproliferative and proapoptotic activities. The present study suggests that the 7-methoxycoumarin nucleus, together with the 3,5-disubstitution pattern of the trans-vinylbenzene moiety, are likely promising structural features to obtain excellent antitumor compounds endowed with a apoptosis-inducing capability. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.069

文献信息

• Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents
  作者：Federica Belluti、Gabriele Fontana、Laura Dal Bo、Nives Carenini、Chiara Giommarelli、Franco Zunino

  DOI：10.1016/j.bmc.2010.03.069

  日期：2010.5

  The naturally occurring coumarins and resveratrol, attract great attention due to their wide range of biological properties, including anticancer, antileukemic, antibacterial and anti-inflammatory activities; moreover, their cancer chemopreventive property have been recently emphasized. A novel class of hybrid compounds, obtained by introducing a substituted trans-vinylbenzene moiety on a coumarin backbone, was synthesized and evaluated for the antitumor profile. A number of derivatives showed a good antiproliferative activity, in some cases higher to that of the reference compound resveratrol. The most promising compounds in this series were 14 and 17, endowed with excellent antiproliferative and proapoptotic activities. The present study suggests that the 7-methoxycoumarin nucleus, together with the 3,5-disubstitution pattern of the trans-vinylbenzene moiety, are likely promising structural features to obtain excellent antitumor compounds endowed with a apoptosis-inducing capability. (C) 2010 Elsevier Ltd. All rights reserved.