Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor.
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.
Khan
Shoeb I
SI
Department of Chemistry, P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina, USA.
Dobrikov
Mikhail I
MI
Shaw
Barbara Ramsay
BR
D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003856:Deoxyuracil Nucleotides / Q000737:chemistry; D003857:Deoxyuridine / Q000737:chemistry; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D005468:Fluorodeoxyuridylate / Q000737:chemistry; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D010165:Palladium / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013940:Thymidylate Synthase / Q000037:antagonists & inhibitors*
D001896:Boron Compounds; D003856:Deoxyuracil Nucleotides; D004791:Enzyme Inhibitors; D010710:Phosphates; D005468:Fluorodeoxyuridylate; D010165:Palladium; D013940:Thymidylate Synthase; D003857:Deoxyuridine