Synthesis of a Small Library of Estradiol-Based Glycosteroid Mimics Containing a Modified D-Ring

FS Ekholm, S Gyula, W Janos, Reko Leino

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    Glycosylated steroids, such as cardenolides and saponins, are widely distributed in nature and have been shown to possess various types of biological activities. In the present study, carbohydrate donors were evaluated for the glycosylation of steroids; the results show that benzoylated imidate donors were superior in terms of efficiency and operational simplicity. These donors were then applied to the synthesis of a limited library of estradiol-based glycosteroid mimics containing a modified D-ring. The deprotected molecules contained three types of variations in the steroid backbone and four types of variations in the sugar moiety. The synthesized structures will be screened for biological activity and for their potential use in drug delivery systems.
    Sidor (från-till)1064–1077
    Antal sidor14
    TidskriftEuropean Journal of Organic Chemistry
    StatusPublicerad - 2011
    MoE-publikationstypA1 Tidskriftsartikel-refererad


    • Glycosylation
    • Steroids

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