Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
Molecules. 2013 Jul 8;18(7):8046-62. doi: 10.3390/molecules18078046.
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 5a-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).
通过两步反应成功合成了氨基蒽醌。首先将 1,4-二羟基蒽醌（1）进行甲基化、还原和酰化，以优异的收率得到蒽-1,4-二酮（3）、1,4-二甲氧基蒽-9,10-二酮（5）和 9,10-二氧代-9,10-二氢蒽-1,4-二基二乙酸酯（7）。用 BuNH2 处理 1、3、5 和 7，并在 PhI(OAc)2 作为催化剂的存在下，得到了七种氨基蒽醌衍生物 1a、b、3a 和 5a-d。3 和 5 的氨化得到了三种新的氨基蒽醌，即 2-(正丁基氨基)蒽-1,4-二酮（3a）、2-(正丁基氨基)蒽-9,10-二酮（5a）和 2,3-(二正丁基氨基)蒽-9,10-二酮（5b）。所有新合成的氨基蒽醌都通过 MTT 测定法对 MCF-7（雌激素受体阳性的人乳腺癌）和 Hep-G2（人肝癌）癌细胞的细胞毒性进行了测试。氨基蒽醌 3a、5a 和 5b 对两种癌细胞系均表现出强烈的细胞毒性（IC50 为 1.1-13.0 µg/mL）。
