6-Substituted 1,4-naphthoquinone oxime derivatives (I): synthesis and evaluation of their cytotoxic activity
6-Substituted 1,4-naphthoquinone oxime derivatives (I): synthesis and evaluation of their cytotoxic activity
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6-取代1,4-萘醌肟衍生物(I)：合成及其细胞毒活性评价
DOI：
10.1007/s00706-016-1899-z
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发表时间：
2017-04
期刊：
影响因子：
--
通讯作者：
Li Shaoshun
中科院分区：
文献类型：
--
作者：
Huang Guang;Zhao Huiran;Zhou Wen;Dong Jinyun;Zhang Qinjing;Meng Qingqing;Zhu Baoquan;Li Shaoshun
合成了一系列6-取代的1,4-萘醌肟衍生物，并对4种癌细胞和1种正常细胞株进行了体外细胞毒性评价。部分化合物对癌细胞表现出中等至良好的细胞毒活性，而所有化合物对正常细胞均无明显的细胞毒活性（IC50 > 100 μM）。在这些肟类衍生物中，有3种化合物对人结肠癌细胞株（HCT-15）的细胞毒性比阿霉素和5-氟尿嘧啶更强，IC50值分别为2.52、1.96和2.27 μM。此外，构效关系研究表明，这些肟衍生物的细胞毒性作用不仅很大程度上取决于R1烷基链的大小，还取决于分支链上取代基R2的大小，这表明这些化合物的强细胞毒性归因于它们适当的亲脂性。本研究为6-取代1,4-萘醌肟衍生物的设计和合成提供了可行的策略。图形抽象
A series of 6-substituted 1,4-naphthoquinone oxime derivatives were synthesized and evaluated for their in vitro cytotoxicity against four cancer cell lines and one normal cell line. Some compounds exhibited moderate to good cytotoxicity towards cancer cells and meanwhile all the synthesized compounds displayed no apparent cytotoxic activity against normal cells (IC50 > 100 μM). Among these oxime derivatives, three compounds showed more potent cytotoxicity against human colon cancer cell lines (HCT-15) than adriamycin and 5-fluorouracil, with an IC50 value of 2.52, 1.96, and 2.27 μM, respectively. Additionally, structure–activity relationship studies revealed that cytotoxic effects of these oxime derivatives were not only largely dependent upon the size of alkyl chain R1, but also upon substituents R2 of the branch chain, indicating that the strong cytotoxicity of these compounds was ascribed to their appropriate lipophilicity. Collectively, this study could provide available strategy for design and synthesis of 6-substituted 1,4-naphthoquinone oxime derivatives as potential anticancer agents.Graphical abstract
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