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Synthesis of 2′-Deoxy-2′-β-fluoro-4′-azido-5-fluorouridine as a Potential Anti-HIV Agent
Synlett ( IF 1.7 ) Pub Date : 2023-12-21 , DOI: 10.1055/a-2213-2408
Jiao Hou 1 , Jian-Hua Wang 2 , Wenquan Yu 1 , Junbiao Chang 1, 2
Affiliation  

2′-Deoxy-2′-β-fluoro-4′-azido-5-fluorouridine, a new pyrimidine nucleoside analogue of azvudine (FNC), was designed and synthesized. The synthesis of this nucleoside analogue was achieved by bromination of 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-d-arabinofuranoside, followed by reaction with silylated 5-fluorouracil and further modifications of the sugar moiety, in a 7.6% overall yield over nine steps. The product exhibited good antiviral activity against HIV-1 infection in HEK293T cells.



中文翻译:

2′-脱氧-2′-β-氟-4′-叠氮基-5-氟尿苷作为潜在抗 HIV 药物的合成

设计并合成了阿兹夫定(FNC)的新型嘧啶核苷类似物2'-脱氧-2'-β-氟-4'-叠氮基-5-氟尿苷。该核苷类似物的合成是通过 1,3,5- O-三苯甲酰基-2-脱氧-2-氟-d-阿拉伯呋喃糖苷,然后与甲硅烷基化的 5-氟尿嘧啶反应并进一步修饰糖部分,经过九个步骤,总产率为 7.6%。该产品对HEK293T细胞中的HIV-1感染表现出良好的抗病毒活性。

更新日期:2023-12-22
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