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  • Title: [(22R,23R)-3beta-Hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one: improved synthesis and toxicity to MCF-7 cells].
    Author: Mekhtiev AR, Timofeev VP, Misharin AIu.
    Journal: Bioorg Khim; 2008; 34(6):840-6. PubMed ID: 19088760.
    Abstract:
    The chemical synthesis of (22R,23R)-3beta-hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one from (22E)-3beta-acetoxy-5alpha-ergosta-7,14,22-triene was improved. The stages of obtaining and isomerizing (22E)-3beta-acetoxy-14alpha,15alpha-epoxy-5alpha-ergosta-7,22-diene were optimized. The introduction of the (22R,23R)-epoxide cycle was carried out by a basic treatment of intermediate (22S,23R)-3beta,23-diacetoxy-22-iodo-5alpha-ergost-8(14)-en-15-one. In cells of human mammary gland carcinoma MCF-7 (22R,23R)-3beta-hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one showed a high toxicity (TC(50) = 0.4 +/- 0.1 microM for 48-h incubation in serum-free medium).
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