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

Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions

1,* email, 1, 2, 3, 3 and 1
Received: 14 May 2013; in revised form: 21 June 2013 / Accepted: 25 June 2013 / Published: 8 July 2013
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

Nor SMM, Sukari MAHM, Azziz SSSA, Fah WC, Alimon H, Juhan SF. Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions. Molecules. 2013; 18(7):8046-8062.

Chicago/Turabian Style

Nor, Siti M.M.; Sukari, Mohd A.H.M.; Azziz, Saripah S.S.A.; Fah, Wong C.; Alimon, Hasimah; Juhan, Siti F. 2013. "Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions." Molecules 18, no. 7: 8046-8062.


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