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  • Title: Substituted adamantylphthalimides: Synthesis, antiviral and antiproliferative activity.
    Author: Mandić L, Benčić P, Mlinarić-Majerski K, Liekens S, Snoeck R, Andrei G, Kralj M, Basarić N.
    Journal: Arch Pharm (Weinheim); 2020 Jun; 353(6):e2000024. PubMed ID: 32285536.
    Abstract:
    In this study, three groups of adamantylphthalimides, bearing different substituents at the phthalimide moiety, N-(4'-R2 )phthalimidoadamantanes (1-7), 3-[N-(4'-R2 )phthalimido]-1-adamantanols (8-10), and 3-[N-(4'-R2 )phthalimido]adamantane-1-carboxylic acids (11-15), were synthesized and screened against tumor cells and viruses. The most potent compounds are not substituted at the adamantane and bear an OH or NH2 substituent at the phthalimide (compounds 3 and 5). The antiproliferative activities of compounds 3 and 5 are in the micromolar range, much higher than the one of thalidomide. A minor antiviral activity against cytomegalovirus and varicella-zoster virus was found for compounds 3 and 5, but these compounds lacked selectivity. The results presented are important for the rational design of the next-generation compounds with anticancer and antiviral activities.
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