Synthesis,cytotoxicity and antiviral activity studies of the conjugates of cobalt bis(1,2-dicarbollide)(-I) with 5-ethynyl-2′-deoxyuridine and its cyclic derivatives |
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Authors: | Anna Ilinova Andrey Semioshkin Irina Lobanova Vladimir I Bregadze Andrey F Mironov Edyta Paradowska Miros?awa Studzińska Agnieszka Jab?ońska Magdalena Bia?ek-Pietras Zbigniew J Le?nikowski |
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Institution: | 1. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia;2. Lomonosov Moscow State University of Fine Chemical Technologies, 86 Vernadskogo Pr., 119571 Moscow, Russia;3. Laboratory of Molecular Virology and Biological Chemistry, Institute of Medical Biology, Polish Academy of Sciences, 106 Lodowa St., 93-232 Lodz, Poland |
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Abstract: | A series of novel conjugates of cobalt bis(1,2-dicarbollide)(-I) with 5-ethynyl-2′-deoxyuridine and its cyclic derivatives were synthesized. Conjugates with 5-ethynyl-2-deoxyuridine were prepared by the direct Sonogashira coupling of a series of cobalt bis(1,2-dicarbollide)(-I) terminal alkynes and 5-iodo-2′-deoxyuridine. Their furo2,3-d]pyrimidin-2(3H)-one isomers were obtained either by intermolecular cyclization of the above conjugates or by Sonogashira coupling using Pd/C as a catalyst. Action of ammonia on these furo2,3-d]pyrimidin-2(3H)-one conjugates resulted in pyrrolo2,3-d]pyrimidin-2(3H)-one conjugates. Most of the designed compounds have shown low cytotoxicity in several cell lines. Some 5-ethynyl-2-deoxyuridine and furo2,3-d]pyrimidin-2(3H)-one conjugates have also presented antiviral activity. |
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Keywords: | 5-Ethynyl-2&prime -deoxyuridine Cobalt bis(1 2-dicarbollide)(-I) Sonogashira coupling Cytotoxicity Antiviral activity |
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