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Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2021-05-26 , DOI: 10.1007/s10593-021-02931-5
Olga V Mikolaichuk 1 , Vladimir V Zarubaev 2 , Anna А Muryleva 2 , Yana L Esaulkova 2 , Daria V Spasibenko 3 , Alina А Batyrenko 3 , Ilya V Kornyakov 1, 4 , Rostislav Е Trifonov 3
Affiliation  

The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, 1H and 13C NMR spectroscopy, high-resolution mass spectrometry, and also by X-ray structural analysis. According to the simultaneous thermal analysis data, the obtained compounds are thermally stable up to a temperature of about 150°C. In vitro studies have shown that some of the 2-adamantyl-5-aryltetrazoles exhibit moderate inhibitory activity against influenza A (H1N1) virus. The antiviral selectivity index (SI) of 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5).



中文翻译:

新型 2-金刚烷基-5-芳基-2H-四唑的合成、结构和抗病毒特性

5-芳基-NH-四唑与金刚烷-1-醇在浓硫酸中的反应区域选择性地进行,形成相应的2-金刚烷基-5-芳基-2 H-四唑。这些化合物的硝化产生 2-(金刚烷-1-基)-5-(3-硝基芳基)-2 H四唑。所获得的新型2-金刚烷基-5-芳基四唑的结构和组成通过红外光谱、1 H和13 C NMR光谱、高分辨率质谱以及X射线结构分析进行了证明。根据同步热分析数据,所得化合物在高达约 150°C 的温度下是热稳定的。体外研究表明,一些 2-金刚烷基-5-芳基四唑对甲型流感 (H1N1) 病毒具有中等抑制活性。2-[2-(adamantan-1-yl)-2 H -tetrazol-5-yl]-6-bromo-4-nitroaniline 的抗病毒选择性指数 (SI) 显着高于参考 (SI 11)药物金刚乙胺(SI 5)。

更新日期:2021-05-26
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