Novel class of amino pyrimidine thioglycoside derivatives were designed from sodium 2-cyano-3-(arylamino)prop-1-ene-1,1-bis(thiolate) 1a-d and guanidine hydrochloride 2 to afford the corresponding sodium 2,6-diamino-5-aryl-1,2-dihydropyrimidine-4-thiolate 3a-d, which in coupling with peracylated α-D-gluco- and galactopyranosyl bromides 5a,b in DMF gave the corresponding pyrimidine thioglycosides 6a-h. Acidification of 2,6-diamino-5-aryl-1,2-dihydropyrimidine-4-thiolate salts 3a-d with hydrochloric acid formed the corresponding pyrimidine-4-thioles 4a-d. The latter were stirred with peracetylated halo sugars α-D-gluco- and galacto-pyranosyl bromides in sodium hydride and DMF to yield the pyrimidine thioglycosides 6a-h. Deacetylation of the pyrimidine thioglycosides gave the corresponding free pyrimidine thioglycosides 7a-h. The compounds were characterized by 13C NMR, 1H NMR, and IR. The pyrimidine thioglycosides 6a-h and free pyrimidine thioglycosides 7a-h were tested against H5N1 virus strain and exhibited high to moderate activity.

中文翻译：

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作为法匹拉韦（avigan）结构类似物的新型嘧啶硫糖苷的合成及其抗禽流感病毒活性

从 2-cyano-3-(arylamino)prop-1-ene-1,1-bis(thiolate) 1a-d 和胍盐酸盐 2 钠 2-cyano-3-(arylamino)prop-1-ene-1a-d 和胍盐酸盐 2 设计了新型氨基嘧啶硫糖苷衍生物，得到相应的钠 2,6-二氨基-5-芳基-1,2-二氢嘧啶-4-硫醇盐3a-d，与DMF中的过酰化α-D-葡糖-和吡喃半乳糖基溴化物5a、b偶联得到相应的嘧啶硫糖苷6a-h。2,6-二氨基-5-芳基-1,2-二氢嘧啶-4-硫醇盐3a-d用盐酸酸化形成相应的嘧啶-4-硫醇4a-d。后者与氢化钠和 DMF 中的全乙酰化卤代糖 α-D-葡糖-和半乳糖-吡喃糖基溴化物一起搅拌以产生嘧啶硫糖苷 6a-h。嘧啶硫糖苷的脱乙酰化得到相应的游离嘧啶硫糖苷 7a-h。化合物通过 13C NMR、1H NMR 和 IR 表征。针对 H5N1 病毒株测试了嘧啶硫糖苷 6a-h 和游离嘧啶硫糖苷 7a-h，并表现出高至中等活性。