新型黄酮半乳糖缀合物的合成与生物活性研究

doi:10.6023/cjoc201210035

有机化学 ›› 2013, Vol. 33 ›› Issue (03): 535-541.DOI: 10.6023/cjoc201210035 上一篇下一篇

研究论文

新型黄酮半乳糖缀合物的合成与生物活性研究

娄定辉, 汪钢强, 夏立, 陈凌, 汪秋安

湖南大学化学化工学院长沙 410082

收稿日期:2012-10-18 修回日期:2012-12-13 发布日期:2012-12-18
通讯作者: 汪秋安 E-mail:wangQA@hnu.edu.cn
基金资助:
湖南省研究生科研创新(No. CX2012B160)和湖南省科技计划(No. 2011FJ3214)资助项目.

Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates

Lou Dinghui, Wang Gangqiang, Xia Li, Chen Ling, Wang Qiuan

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2012-10-18 Revised:2012-12-13 Published:2012-12-18
Supported by:
Project supported by the Hunan Provincial Innovation Foundation for Postgraduate (No. CX2012B160) and the Science and Technology Planning Project of Hunan Province (No. 2011FJ3214).

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摘要/Abstract

以香叶木素或野漆树苷为原料, 经过O-甲基化、酸性水解、O-苄基化和过氧丙酮(DMDO)氧化等反应步骤, 合成了5,7,3',4'-四甲氧基黄酮醇(1), 5,7,3'-三苄氧基-4'-甲氧基黄酮醇(2), 5,7,4'-三甲氧基黄酮醇(3), 金合欢素(4)和5,7-二羟基- 4'-苄氧基黄酮(5), 运用“点击化学”方法, 将所合成黄酮类的炔基化合物6～10与β-叠氮化乙酰基半乳糖通过铜催化的1,3-偶极环加成反应链接起来, 合成了一系列未见文献报道的新型黄酮半乳糖缀合物11～20. MTT蛋白染色法体外抗肿瘤细胞生物活性测试发现, 化合物11, 13和20对白血病细胞(HL-60)、肝癌细胞(SMMC-7721)、乳腺癌细胞(MCF-7)、结肠癌细胞(SW480)和肺癌细胞(A-549)具有一定的抑制活性.

Five flavonoids 5,7,3',4'-tetramethoxyflavonol (1), 5,7,3'-tribenzyloxy-4'-methoxy flavonol (2), 5,7,4'-trimethoxy- flavonol (3), acacetin (4) and 5,7-dihydroxy-4'-benzyloxyflavone (5) were synthesized from diosmetin or rhoifolin by O-methylation, dehydrogenation, glycoside hydrolysis, O-benzylation and dimethyldioxirane (DMDO) oxidation. Based on “Click chemistry”, ten novel flavonoids galactoconjugates 11～20 were synthesized in good yield using copper-mediated 1,3-dipolar cycloaddition reactions of acetylgalactose azides and alkynyl-substituted flavonoids 6～10. Their biological activities against five human cancer cell lines were evaluated by the standard MTT method. The results showed that 11, 13 and 20 exhibited moderate cytotoxicity against HL-60, SMMC-7721, MCF-7, SW480 and A-549 cancer cell lines.

Key words: flavonoids, galactoconjugates, Click chemistry, synthesis, biological activity

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娄定辉, 汪钢强, 夏立, 陈凌, 汪秋安. 新型黄酮半乳糖缀合物的合成与生物活性研究[J]. 有机化学, 2013, 33(03): 535-541.

Lou Dinghui, Wang Gangqiang, Xia Li, Chen Ling, Wang Qiuan. Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates[J]. Chin. J. Org. Chem., 2013, 33(03): 535-541.

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新型黄酮半乳糖缀合物的合成与生物活性研究

Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates

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