8-alyl-2-[2-methoxybenzylidene]-4-methoxyfuro[3,2-f][1]benzofuran-3(2H)-one | 1616883-71-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 8-alyl-2-[2-methoxybenzylidene]-4-methoxyfuro[3,2-f][1]benzofuran-3(2H)-one
• 英文别名: 4-methoxy-2-[(2-methoxyphenyl)methylidene]-8-prop-2-enylfuro[3,2-f][1]benzofuran-3-one
• CAS: 1616883-71-6
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: JHMHJENYFQVKFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-(7-allyl-6-hydroxy-4-methoxybenzofuran-5-yl)-3-(2-methoxyphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到8-alyl-2-[2-methoxybenzylidene]-4-methoxyfuro[3,2-f][1]benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents

  摘要：

  Various flavonoid scaffold based derivatives viz furochalcones (3a-e, 6a-d and 9a-d), furoflavones (10a-d, 11a-d,12a-d,18a&b), flavones (21a-d), furoaurones (13a,b,14a-d and 15a-d) and 7-styrylfurochromones (22a-d and 25a-e) were designed and synthesized. The novel compounds were evaluated for their anti-proliferative activity against a panel of 60 cancer cell lines comprising 9 types of tumors. Ten compounds belonging to the major subgroups of flavonoids viz furochalcones (3a, 3d, 6b, 9a and 9b), furoflavones (12a and 12c), furoaurones (15d), styrylfurochromones (25b and 25e) showed very promising activity. These active compounds were also evaluated in vitro as kinase inhibitors against CDK2/cyclin E1, CDK4/cyclin D1 and GSK-3 beta and the best inhibition was displayed against GSK-3 beta with the allylfurochalcone derivative 9b exhibiting 80% decrease in GSK-3 beta catalytic activity. On the other hand, the styrylfurochromone 25e interestingly showed a 13% enhancement of GSK-3 beta catalytic power and a 12% reduction in CDK4/cyclin D1 activity. Finally, the in vivo anti-tumor activity of 25e was evaluated against breast cancer induced in mice. The results showed a profound anti-tumor effect of 25e that accompanies a significant increase and decrease in the levels of GSK-3 beta and cyclin D1, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.007