Abstract

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).

Highlights

  • The synthesis of aminoanthraquinone derivatives was achieved through two simple reaction steps

  • The results proved that the amination occurred via a nucleophilic substitution reaction and in agreement with reported works [21,25]

  • Aminoantraquinone derivatives were synthesised through methylation, reduction or acylation followed by amination

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Summary

Introduction

It has been reported that amino-substituted anthraquinones show significantly increased antiproliferative activities against human/mammalian cancer cell lines [21,22] and are known to have potential antitumor activity, but are less toxic to normal cells and display low cardiotoxicity [23,24,25,26]. A study on 4-(N-cyclohexylamino)-emodin implied that it can discriminate well between hepatoma cells and primary hepatocytes and it retained the capacity to reverse the multi-drug-resistance phenotype [27]. Other aminoanthraquinone derivatives such as Reactive Blue 2 (RB-2), Acid Blue 25. The potential of RB-2 was driven by its hydrophobic interactions of aromatic -electron systems, and the hydrogen bonds with nitrogen as donor and acceptor atoms as these properties could block the P2-recptor

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