Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor |
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Authors: | Khan Shoeb I Dobrikov Mikhail I Shaw Barbara Ramsay |
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Institution: | Department of Chemistry, P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina, USA. |
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Abstract: | The 5-ethynyl-2'-deoxyuridine nucleoside and the 5'-boranomonophosphate nucleotide were synthesized as analogs of 5-fluoro-2'-deoxyuridine monophosphate (5-FdUMP), a widely used mechanism-based inhibitor of thymidylate synthase. Synthesis was carried out from protected 5-iodo-2'-deoxyuridine and trimethylsilylacetylene by Sonogashira palladium-catalyzed cross coupling reaction followed by selective phosphorylation and finally boronation. |
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