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

Akhtar, Muhammad Nadeem and Seema, Zareen and Swee, Keong Yeap and Wan, Yong Ho and Kong, Mun Lo and Hasan, Aurangzeb and Noorjahan Banu, Alitheen (2013) Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues. Molecules, 18 (8). pp. 10042-10055. ISSN 1420-3049 (print); 1420-3049 (online)

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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 µg/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.

Item Type: Article
Additional Information: IF: 2.428
Uncontrolled Keywords: Anthraquinone; Damnacanthal; Nordamnacanthal; MCF-7; K-562; Cytotoxic effects
Subjects: Q Science > QD Chemistry
Faculty/Division: Faculty of Industrial Sciences And Technology
Depositing User: PM. Dr. Muhammad Nadeem Akhtar
Date Deposited: 27 Mar 2014 08:20
Last Modified: 18 Apr 2018 04:14
URI: http://umpir.ump.edu.my/id/eprint/5262
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