Substituted adamantylphthalimides: Synthesis,antiviral and antiproliferative activity |
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Authors: | Leo Mandić Patricia Benčić Kata Mlinarić-Majerski Sandra Liekens Robert Snoeck Graciela Andrei Marijeta Kralj Nikola Basarić |
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Affiliation: | 1. Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia;2. Division of Molecular Medicine, Ruđer Bošković Institute, Zagreb, Croatia;3. Laboratory of Virology and Chemotherapy, Rega Institute, KU Leuven, Leuven, Belgium |
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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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Keywords: | adamantane antiproliferative activity antiviral activity phthalimide |
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