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Molecules 2013, 18(8), 10042-10055; doi:10.3390/molecules180810042

Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues

1
Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak 26300, Kuantan Pahang, Malaysia
2
Institute of Bioscience, Universiti Putra Malaysia, UPM Serdang 43400, Selangor Darul Ehsan, Malaysia
3
School of Biomedical Sciences, The University of Nottingham Malaysia Campus, Jalan Broga, Semenyih 43500, Selangor, Malaysia
4
Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia
5
Faculty of Biotechnology and Bimolecular Sciences, Universiti Putra Malaysia, UPM Serdang 43400, Selangor Darul Ehsan, Malaysia
*
Author to whom correspondence should be addressed.
Received: 22 May 2013 / Revised: 29 June 2013 / Accepted: 16 July 2013 / Published: 20 August 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
Keywords: Anthraquinone; damnacanthal; nordamnacanthal; MCF-7; K-562; cytotoxic effects Anthraquinone; damnacanthal; nordamnacanthal; MCF-7; K-562; cytotoxic effects
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MDPI and ACS Style

Akhtar, M.N.; Zareen, S.; Yeap, S.K.; Ho, W.Y.; Lo, K.M.; Hasan, A.; Alitheen, N.B. Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues. Molecules 2013, 18, 10042-10055.

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