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. 2013 Aug 20;18(8):10042-55.
doi: 10.3390/molecules180810042.

Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Muhammad Nadeem Akhtar  1 , Seema Zareen, Swee Keong Yeap, Wan Yong Ho, Kong Mun Lo, Aurangzeb Hasan, Noorjahan Banu Alitheen
Affiliations

Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Muhammad Nadeem Akhtar et al. Molecules. .

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.

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Figures

Figure 1
Figure 1
The ORTEP diagram of 2-bromomethyl-1,3-dimethoxy-9,10-athraquinone (5).
Scheme 1
Scheme 1
Reactions pathway for synthesis of nordamnacanthal (2).
Scheme 2
Scheme 2
Reactions pathway for synthesis of damnacanthal (1).
Figure 2
Figure 2
Structure of compounds 13a to 13h.
See this image and copyright information in PMC

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