Citation: . Cerium (Ⅳ) ammonium nitrate (CAN)-mediated regioselective synthesis and anticancer activity of 6-substituted 5, 8-dimethoxy-1, 4-naphthoquinone[J]. Chinese Chemical Letters, ;2017, 28(7): 1553-1558. doi: 10.1016/j.cclet.2016.10.034 shu

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

Received Date: 28 June 2016
Revised Date: 4 September 2016
Accepted Date: 30 September 2016
Available Online: 3 July 2016

Figures(4)

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.
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