Next Article in Journal
In-Solution Conformational Analysis of the XCYCH3 Moiety for Small Esters and Ethers with all Combinations of X, Y = O, S
Previous Article in Journal
Mechanistic Studies on Regioselective Dephosphorylation of Phosphate Prodrugs during a Facile Synthesis of Antitumor Phosphorylated 2-Phenyl-6,7-methylenedioxy-1H-quinolin-4-one
Article Menu

Export Article

Open AccessArticle
Molecules 2013, 18(7), 8046-8062; https://doi.org/10.3390/molecules18078046

Synthesis of New Cytotoxic Aminoanthraquinone Derivatives via Nucleophilic Substitution Reactions

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 Chemistry)
Full-Text   |   PDF [301 KB, uploaded 18 June 2014]   |  

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). View Full-Text
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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top