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  • The design, synthesis, and anti-inflammatory evaluation of a drug-like library based on the natural product valerenic acid

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    Davis142802-Accepted.pdf (494.2Kb)
    File version
    Accepted Manuscript (AM)
    Author(s)
    Egbewande, Folake A
    Nilsson, Niclas
    White, Jonathan M
    Coster, Mark J
    Davis, Rohan A
    Griffith University Author(s)
    Davis, Rohan A.
    Coster, Mark J.
    Egbewande, Folake A.
    Year published
    2017
    Metadata
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    Abstract
    The plant natural product, valerenic acid (1) was chosen as a desirable scaffold for the generation of a novel screening library due to its drug-like physicochemical parameters (such as Log P, hydrogen bond donor/acceptor counts, and molecular weight). An 11-membered amide library (2–12) was subsequently generated using parallel solution-phase synthesis and Ghosez’s reagent. The chemical structures of all semi-synthetic analogues (2–12) were elucidated following analysis of the NMR, MS, UV and IR data. The structures of compounds 8 and 11 were also confirmed by X-ray crystallographic analysis. All library members were evaluated ...
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    The plant natural product, valerenic acid (1) was chosen as a desirable scaffold for the generation of a novel screening library due to its drug-like physicochemical parameters (such as Log P, hydrogen bond donor/acceptor counts, and molecular weight). An 11-membered amide library (2–12) was subsequently generated using parallel solution-phase synthesis and Ghosez’s reagent. The chemical structures of all semi-synthetic analogues (2–12) were elucidated following analysis of the NMR, MS, UV and IR data. The structures of compounds 8 and 11 were also confirmed by X-ray crystallographic analysis. All library members were evaluated for their ability to inhibit the release of IL-8 and TNF-α. Six analogues showed moderate activity in the IL-8 assay with IC50 values of 2.8–8.3 μM, while none of the tested compounds showed any significant effect on inhibiting TNF-α release.
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    Journal Title
    Bioorganic & Medicinal Chemistry Letters
    Volume
    27
    DOI
    https://doi.org/10.1016/j.bmcl.2017.05.021
    Copyright Statement
    © 2017 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
    Medicinal and biomolecular chemistry
    Organic chemistry
    Organic chemistry not elsewhere classified
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/341995
    Collection
    • Journal articles

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