新型喹唑啉酮类查尔酮的合成及体外细胞毒性评价

Trương Thuc Bao Nguyen, Ta Hong Duc, T. Vu
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引用次数: 0

摘要

查尔酮是一类具有广泛生物活性的化合物。此外,基于喹唑啉酮骨架的衍生物是目前筛选具有细胞毒性作用的化合物的研究热点。在喹唑啉酮的基础上含有查尔酮结构的化合物可以产生具有细胞毒作用的新结构。本文采用三步法合成了新的喹唑啉酮类查尔酮8a-j。第一步是5-羟基苯甲酸(5)与乙酸酐在回流下缩合2小时,得到中间体6(87%)。然后将该中间体与4-氨基苯乙酮在乙酸中回流反应14小时,得到7 / 77%。最后,在NaOH存在下,7与不同醛在乙醇中室温反应14h,得到目标化合物8a-j的比例为57 - 75%。合成化合物的结构通过1H、13C NMR和MS谱进行了确证。生物实验结果表明,几种化合物对HepG-2和SKLu-1两种细胞系具有细胞毒活性。其中8c对SKLu-1的细胞毒活性最强,IC50值为20.10µM。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis and In vitro Cytotoxic Evaluation of New Quinazolinone-Based Chalcones
Chalcones are a class of compounds with a wide range of biological activities. In addition, derivatives based on the quinazolinone skeleton are currently of interest to research in the screening of compounds with cytotoxic effects. Compounds containing chalcone structures on the basis of quinazolinone can yield new structures with cytotoxic effects. This article presents the synthesis of new quinazolinone-based chalcones 8a-j via a three step-procedure. The first step is the condensation of 5-hydroxyanthranilic acid (5) with acetic anhydride at reflux for 2 h to afford intermediate 6 in 87%. This intermediate was then reacted with 4-aminoacetophenone in acetic acid at reflux for 14 h to give 7 in 77 %. Finally, the reaction of 7 with different aldehydes in ethanol in the presence of NaOH at room temperature for 14 h furnished target compounds 8a-j in 57 - 75%. The structure of synthesized compounds was confirmed using 1H, 13C NMR and MS spectra. The bioassay results showed that several compounds displayed cytotoxic activity against two cell lines including HepG-2 and SKLu-1. Among synthesized compounds, 8c exhibited the strongest cytotoxic activity against SKLu-1 with IC50 value of 20.10 µM.
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