Publication: Unified synthesis and cytotoxic activity of 8-O -methylfusarubin and its analogues
Issued Date
2019-01-01
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ISSN
14770520
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2-s2.0-85069757821
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Mahidol University
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.17, No.29 (2019), 7078-7087
Suggested Citation
Pongsit Vijitphan, Vatcharin Rukachaisirikul, Chatchai Muanprasat, Panata Iawsipo, Jiraporn Panprasert, Kwanruthai Tadpetch Unified synthesis and cytotoxic activity of 8-O -methylfusarubin and its analogues. Organic and Biomolecular Chemistry. Vol.17, No.29 (2019), 7078-7087. doi:10.1039/c9ob01221d Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/50359
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Title
Unified synthesis and cytotoxic activity of 8-O -methylfusarubin and its analogues
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Abstract
© 2019 The Royal Society of Chemistry. A simple and unified synthesis of four related pyranonaphthoquinone natural products, e.g. 8-O-methylfusarubin, 8-O-methylanhydrofusarubin, fusarubin and anhydrofusarubin, is reported. The key synthetic features include the precedented Diels-Alder cycloaddition to assemble the naphthalene skeleton, selective formylation and acetonylation and intramolecular acetalization to construct the pyran ring. Manipulation of the oxidation state of the naphthoquinone core was performed to construct the two analogues, fusarubin and anhydrofusarubin. This work also highlights an unprecedented directing effect of the hydroxymethylene group in the selective hypervalent iodine-mediated quinone oxidation. The four synthetic compounds were evaluated for their in vitro cytotoxic activities against six human cancer cells. 8-O-Methylfusarubin was the most potent analogue and displayed excellent cytotoxic activity against MCF-7 breast cancer cells with an IC50 value of 1.01 μM with no cytotoxic effect on noncancerous Vero cells, which could potentially be a promising lead compound for anti-breast cancer drug discovery.