Cerium（Ⅳ） ammonium nitrate（CAN）-mediated regioselective synthesis and anticancer activity of 6-substituted 5,8-dimethoxy-1,4-naphthoquinone

6-Substituted 5,8-O-dimethyl-1,4-naphthoquinones（6-DMNQ）,the promising anticancer scaffolds,were selectively generated by oxidative demethylation of 2-substituted 1,4,5,8-tetramethoxynaphthalenes with CAN in EtOAc/H2O in comparatively high yields.An interesting finding was that apart from the report...

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Published in:中国化学快报：英文版 2017, Vol.28 (7), p.1553-1558
Main Author: Guang Huang Hui-Ran Zhao Qing-Qing Meng Wen Zhou Qi-Jing Zhang Jin-Yun Dong Jia-Hua Cui Shao-Shun Li
Format: Article
Language:English
Subjects:
CAN
介导
抗癌活性
硝酸铵
空间位阻效应
细胞毒性
选择性合成
铈（Ⅳ）
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Summary:6-Substituted 5,8-O-dimethyl-1,4-naphthoquinones（6-DMNQ）,the promising anticancer scaffolds,were selectively generated by oxidative demethylation of 2-substituted 1,4,5,8-tetramethoxynaphthalenes with CAN in EtOAc/H2O in comparatively high yields.An interesting finding was that apart from the reported electron-withdrawing effects of substituents on position 2 of naphthalene ring,regioselective synthesis of 6-DMNQ was largely dependent on the steric effects in CAN-mediated oxidation.The selective cytotoxicities of 6-DMNQ from the in vitro cell-based assays were exhibited between the cancer cells and normal cells.Moreover,most of sulfur-containing 6-DMNQ derivatives displayed better anticancer activities than the corresponding oxygen-containing ones,which could provide an available strategy for the design of 6-DMNQ derivatives as potential anticancer agents.
ISSN:1001-8417
1878-5964