Abstract Some 5-substituted ribavirin analogues have a high antiviral and anticancer activity, but their mechanisms of action are obviously not the same as their parent compound. The SAR studies performed on 3 (5)-substituted 1,2,4-triazole nucleosides have shown a high dependency between the structure of the 3 (5)-substituent and the level of antiviral/anticancer activity. The most active substances of the row contain coplanar with the 1,2,4-triazole ring aromatic substituent which is connected by a rigid ethynyl bond. However, the compounds with the trans-vinyl linker also had antiviral activity. We decided to study the antitumor activity of ribavirin analogues with alkyl/aryl vinyl substituents in the 5th position of the 1,2,4-triazole ring. Protected nucleoside analogues with various 5-alkylvinyl substituents were obtained by Horner-Wadsworth-Emmons reaction from the common precursor and converted to the nucleosides. Arylvinyl nucleosides were synthesised according the reported procedures. All compounds did not show significant antiproliferative activity on several tumour cell lines. Coplanar aromatic motif in the 5-substituent for the anticancer activity manifestation was confirmed.

中文翻译：

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5-烷基乙烯基-1,2,4-三唑核苷：合成和生物学评价

摘要 一些5-取代利巴韦林类似物具有较高的抗病毒和抗癌活性，但其作用机制与母体明显不同。对 3 (5)-取代的 1,2,4-三唑核苷进行的 SAR 研究表明，3 (5)-取代基的结构与抗病毒/抗癌活性水平之间存在高度依赖性。该行中最活跃的物质包含与 1,2,4-三唑环芳族取代基共面的物质，该取代基通过刚性乙炔键连接。然而，具有反式乙烯基接头的化合物也具有抗病毒活性。我们决定研究在 1,2,4-三唑环的第 5 位具有烷基/芳基乙烯基取代基的利巴韦林类似物的抗肿瘤活性。通过霍纳-沃兹沃思-埃蒙斯反应从普通前体获得具有各种 5-烷基乙烯基取代基的受保护核苷类似物并转化为核苷。根据报道的程序合成芳乙烯基核苷。所有化合物对几种肿瘤细胞系均未显示出显着的抗增殖活性。证实了抗癌活性表现的 5-取代基中的共面芳香基序。