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  • Synthesis of bilocularin A carbamate derivatives and their evaluation as leucine transport inhibitors in prostate cancer cells

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    Davis439959-Accepted.pdf (706.5Kb)
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    Accepted Manuscript (AM)
    Author(s)
    Huxley, C
    Wibowo, M
    Lum, KY
    Gordon, S
    D'Hyon, S
    Guan, H
    Wang, X
    Chen, Y
    Si, M
    Wang, M
    White, JM
    Wahi, K
    Wang, Q
    Holst, J
    Davis, RA
    Griffith University Author(s)
    Davis, Rohan A.
    Year published
    2020
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    Abstract
    Large-scale extraction of the leaves of the Australian rainforest tree Maytenus bilocularis followed by extensive purification studies afforded the targeted and abundant dihydro-β-agarofuran, bilocularin A, in sufficient quantities (>500 mg) for detailed semi-synthetic chemistry. Eight bilocularin A carbamate analogues were synthesised using a series of commercially available isocyanate reagents in high purity (>95%) and variable yields (9–91%). All previously undescribed analogues were spectroscopically characterised using NMR, UV, IR and MS data. One compound afforded crystalline material and subsequent single crystal X-ray ...
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    Large-scale extraction of the leaves of the Australian rainforest tree Maytenus bilocularis followed by extensive purification studies afforded the targeted and abundant dihydro-β-agarofuran, bilocularin A, in sufficient quantities (>500 mg) for detailed semi-synthetic chemistry. Eight bilocularin A carbamate analogues were synthesised using a series of commercially available isocyanate reagents in high purity (>95%) and variable yields (9–91%). All previously undescribed analogues were spectroscopically characterised using NMR, UV, IR and MS data. One compound afforded crystalline material and subsequent single crystal X-ray analysis (Cu-Kα) confirmed the chemical structure along with the absolute configuration. All compounds were evaluated for anti-proliferative activity against the human prostate cancer cell line LNCaP; none of the compounds showed significant (>50%) growth inhibition at 20 μM. Compounds were also tested for their ability to inhibit leucine transport in LNCaP cells, and two analogues showed moderate activity with IC50 values of 8.9 and 8.5 μM. This is the first reported synthesis of dihydro-β-agarofuran carbamate derivatives.
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    Journal Title
    Phytochemistry
    Volume
    179
    DOI
    https://doi.org/10.1016/j.phytochem.2020.112478
    Copyright Statement
    © 2020 Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence (http://creativecommons.org/licenses/by-nc-nd/4.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.
    Subject
    Chemical sciences
    Biological sciences
    Biomedical and clinical sciences
    Bilocularin A
    Carbamate
    Celastraceae
    Dihydro-β-agarofuran
    LNCaP
    Publication URI
    http://hdl.handle.net/10072/396933
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    • Journal articles

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