Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2 H -tetrazoles
The reaction of 5-aryl- -tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2 -tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2 tetrazoles. The structures and composit...
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Published in | Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 57; no. 4; p. 442 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
Published |
United States
2021
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Subjects | |
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Abstract | The reaction of 5-aryl-
-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2
-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2
tetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy,
H and
C 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.
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)-2
-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5).
The online version contains supplementary material available at 10.1007/s10593-021-02931-5. |
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AbstractList | The reaction of 5-aryl-
-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2
-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2
tetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy,
H and
C 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.
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)-2
-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5).
The online version contains supplementary material available at 10.1007/s10593-021-02931-5. |
Author | Muryleva, Anna А Trifonov, Rostislav Е Batyrenko, Alina А Spasibenko, Daria V Esaulkova, Yana L Kornyakov, Ilya V Zarubaev, Vladimir V Mikolaichuk, Olga V |
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Keywords | X-ray structural analysis anti-influenza activity nitration 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles adamantylation |
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-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding... |
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Title | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2 H -tetrazoles |
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