Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor.
Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor.
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合成 5-乙炔基-2-脱氧尿苷-5-硼单磷酸作为潜在的胸苷酸合成酶抑制剂。
DOI：
10.1081/ncn-200060046
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Shaw,BarbaraRamsay
中科院分区：
文献类型：
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作者：
Khan,ShoebI;Dobrikov,MikhailI;Shaw,BarbaraRamsay
5-氟-2 ′-脱氧尿苷单磷酸（5-FdUMP）是一种广泛使用的基于机理的胸苷酸合成酶抑制剂，合成了5-乙炔基-2 ′-脱氧尿苷核苷和5′-硼单磷酸核苷类似物。以保护的5-碘-2 ′-脱氧尿苷和三甲基硅基乙炔为原料，经Sonogashira钯催化的交叉偶联反应，选择性磷酸化，最后硼化合成了5-碘-2 ′-脱氧尿苷。
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.