Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (>1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (>3), 1,4-dimethoxyanthracene-9,10-dione (>5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (>7). Treatment of >1, >3, >5 and >7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives >1a, >b, >3a, and >5>a–>d. Amination of >3 and >5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (>3a), 2-(butylamino)anthracene-9,10-dione (>5a) and 2,3-(dibutylamino)anthracene-9,10-dione (>5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones >3a, >5a and >5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1–13.0 µg/mL).
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