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Molecules 2013, 18(7), 8046-8062; doi:10.3390/molecules18078046
Article

Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions

1,* , 1, 2, 3, 3 and 1
1 Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia 2 Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia 3 Department of Biology, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia
* Author to whom correspondence should be addressed.
Received: 14 May 2013 / Revised: 21 June 2013 / Accepted: 25 June 2013 / Published: 8 July 2013
(This article belongs to the Section Organic Synthesis)
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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 5ad. 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).
Keywords: methylation; reduction; acylation; amination; substitution; aminoanthraquinone; mechanism; cytotoxic; MCF-7; Hep-G2 methylation; reduction; acylation; amination; substitution; aminoanthraquinone; mechanism; cytotoxic; MCF-7; Hep-G2
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Nor, S.M.M.; Sukari, M.A.H.M.; Azziz, S.S.S.A.; Fah, W.C.; Alimon, H.; Juhan, S.F. Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions. Molecules 2013, 18, 8046-8062.

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