(E)-7-methoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one | 1401428-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-7-methoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one
• 英文别名: 7-methoxy-2-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]chromen-4-one
• CAS: 1401428-03-2
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: ZIELBSWDVHGGFO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-7-methoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以34.7%的产率得到(E)-7-hydroxy-2-(3,4,5-trihydroxystyryl)-4H-chromen-4-one
  参考文献：
  名称：

  Structure–activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

  摘要：

  The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI(50) value of 1.3 mu M. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.

  DOI：

  10.1007/s00044-012-0232-6
• 作为产物：
  描述：

  7-methoxy-2-methyl-chromen-4-one 、 3,4,5-三甲氧基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以75%的产率得到(E)-7-methoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one
  参考文献：
  名称：

  Structure–activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

  摘要：

  The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI(50) value of 1.3 mu M. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.

  DOI：

  10.1007/s00044-012-0232-6

文献信息

• Structure–activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells
  作者：Chen Lin、Pei-Jung Lu、Chia-Ning Yang、Christopher Hulme、Arthur Y. Shaw

  DOI：10.1007/s00044-012-0232-6

  日期：2013.5

  The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI(50) value of 1.3 mu M. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.