| 第 51 卷第 6 期 |  | Vol. 51 No. 6 | | 2021 年 12 月 | Dec 2021 |
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所属栏目：医药及中间体
3-甲氧基黄酮的合成及抗肿瘤活性研究 |
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孙世猷， 姜晓晔， 王 璇
（武汉城市学院 医学部， 胡北 武汉 430083)
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| 摘 要：以 2-经基苯甲酴（4）为原籵， 在氢氧化钾催化下， 与 3-甲氧基苯乙酮（3）反应制得 1-（2-经基苯
基）-3-（3-甲氧基苯基）-2-丙烯酮 （2）， 2 在 I2 / DMSO 体系中发生氧化关环反应得到 3'-甲氧基黄酮 （1），产品结构通过核磁共振氢谱进行了表征确证。 优化了反应条件：
在第一步经酴缩合反应中， 氢氧化钾为催化剂， n（2-经基苯甲酴）:n（氢氧化钾）=1:5； 在 2-经基查耳酮的氧化关环反应中：
n（1-（2-经基苯基）-3-（3-甲氧基苯基）-2-丙烯酮）:n（殃）=1.00:0.15， 反应溶剂为二甲基亚巩， 85 °C反应 24 h。 优化条件下产物总收率为 82.2%。 此外，
采用 MTS 法测试了 3'-甲氧基黄酮（1）对 MCF-刁、 PC-3、 HepG2、 HeLa 和 A549 五种肿瘤细胞的抑制活性。 结果表明， 3'-甲氧基黄酮
（1）对五种肿瘤细胞均表现良好的抑制活性， 尤其是对
HepG2 有最强的抑制活性， 其 IC50=11.3土1.4 μ.mol / L， 为进一步开发具有抗肿瘤活性的3'-甲氧基黄酮类化合物提供参考。
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| 关键词：
3'-甲氧基黄酮； 查耳酮； 抗肿瘤活性
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| 中图分类号：TQ463 文献标识码：A 文章编号：1009-9212(2021)06-0027-05 |
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Synthesis and Anti-tumor Activity Evaluation of 3'-Methoxyl flavone
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SUN Shi一you, JIANG Xiao一ye, WANG Xuan
(School of Medicine, Wuhan City College, Wuhan 430083, China)
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| Abstract：2-Hydroxybenzaldehyde (4) was used as raw material, and reacted with
3-methoxyacetophenone (3) to
obtain (E)-3 -(3 -methoxyphenyl)-1 -(2 -hydroxyphenyl)prop-2 -en-1 -one (2) under the catalysis of
potassium hydroxide. Subsequently, oxidative cyclization of compound 2 in the presence of catalytic
amount of iodine and concentrated sulfuric acid in DMSO afforded 3'-methoxyl flavone (1). The
structure of the product 1 was confirmed by 1H NMR. Meanwhile, the reaction conditions were
optimized: in the first step aldol condensation, potassium
hydroxide was used as catalyst; n （2 -hydroxybenzaldehyde) :n (KOH) =1 :5; in the oxidative
cyclization of 2' - hydroxychalcone,
n((E)-3-(3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one):n(Iodine)=1.00:0.15; DMSO was used as
solvent; reaction was set at 85°C for 24 h. Under optimal conditions, the total yield of
3'-methoxyl
flavone (1) was 82.2%. Moreover, the antitumor activity against MCF-7, PC-3, HepG2, HeLa and A549
of target compound 1 was tested by MTS assay. The preliminary biological results indicated that 3'
-methoxyl flavone (1) showed potent inhibitory activities against MCF-7, PC-3, HepG2, HeLa and A549
cells, especially to HepG2, which showed strong inhibitory effect with a IC50 value of 11.3扛1.4
μ.mol/L. These results could provide reference for the further development of 3'-methoxyl flavone
(1) derivative as anti-tumor agents.
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| Key words：
3'-methoxyl flavone; chalcone; anti-tumor activity
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作者简介：
孙世猷(1989—)，男，山东成武人，硕士，主要从事药物开发生物材料研究。
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收稿日期：2021-10-12
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