Synthesis and antiviral activity of [(9-R1-10-R2-3-R-2-oxo-2H-[1,2,4]-triazino[2,3-c]quinazolin-6-yl)thio]acetamides derivatives with the fragments of carcass amines

I. S. Nosulenko, O. Yu. Voskoboynik, G. G. Berest, S. L. Safronyuk, S. I. Kovalenko, A. V. Katsev, R. S. Sinyak, V. O. Palchikov


Alkylation of potassium 9-R1-10-R2-3-R-2-oxo-2Н-[1,2,4]triazino[2,3 с]quinazolin-6-thiolates by N-cycloalkyl-(cycloalkylaryl-)-2-chloracetamides and interaction of [(9-R1-10-R2-3-R-2-оxo-2H-[1,2,4]triazino[2,3-с]quinazolin-6-yl) thio]acetiс acids imidazolides and chloranhydrides with carcass amines yielded the corresponding amides. The structures of the compounds synthesized have been confirmed by 1H, 13C NMR, LC–MS and EI-MS analysis.
The features of 1H, 13C NMR, LC–MS and EI-MS spectra have been described, and characteristic signals have been identified. The compounds synthesized have been studied for their antiviral activity. The results of the antiviral assay have shown that some compounds exhibit a moderate and high activity against the strains studied.
The correlation between the structure and the antiviral action has been also discussed. According to the data obtained the conclusion can be made that the combination of carcass amine moieties with the fragment of little known [(9-R1-10-R2-3-R-2-оxo-2H-[1,2,4]-triazino[2,3-с]quinazolin-6-yl)thio]асetic acid results in compounds with a high antiviral activity. High indicators of the antiviral activity of compounds 3.2 and 3.14 against Influenza Type A H3N2 allow to suppose the expediency of further chemical modification of [1,2,4]triazino[2,3-с]quinazoline directed to obtaining new antiviral agents.


2-[(9-R1-10-R2-3-R-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides; carcass amines; viruses Flu A&B strain; antiviral activity

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2. Morozov I. S., Petrov V. I., Sergeev S. A. Farmakologiya adamantanov – Pharmacology of adamantines, Volgograd, 2001, 320 p.

3. Geldenhuys W. J., Malan S. F., Bloomquist J. R., Marchand A. P., Van der Schyf C. J. Med. Res. Rev., 2005, Vol. 25, pp.21-48. doi: 10.1002/med.20013

4. Pat. US 20130231391 A1 Adamantane derivatives possessing anti-viral and anti-microbial activity, B.Vithal Shetty; Vymed Corporation (USA),
Application Date: 15.02.2013, Publication Date: 05.08.2013.

5. Leonova M. V., Golovin E. V., Shiriaev A. K., Savinova O. V., Klimochkin Yu. V., Skomorohov M. Yu. Kuznetsov S. A. “Aminoderivatives of adamantine with antiviral activity against influenza viruses”, Pat. of Russian Federation №2401263.

6. Buagergen R., Burry B., Burry M., Kazella P., Erber J. M., Ler P., Nizato P., Raymon P., Verner J. “Benzene derivatives, methods of their preparation and pharmaceutical composition with their content”, Pat. of Russian  Federation №2248964, Application Date: 08.06.2000, Publication Date: 10.09.2003.

7. Bernardon J.-M. “Bicyclic aromatic compounds and baised on them composition”, Pat. of Russian Federation №2188190, Application Date 30.03.1999, Publication Date 27.02.2002.

8. Berest G. G., Voskoboynik O. Yu., Kovalenko S. I., Nosulenko I. S., Antypenko L. M., Antypenko O. M., Shvets V. M., Katsev A. M. Sci. Pharm., 2012, Vol. 80, pp.37-65. doi:10.3797/scipharm.1111-15

9. Kovalenko S. I., Nosulenko I. S., Voskoboynik A. Yu., Berest G. G., Antypenko L. M., Antipenko A. N., Katsev A. M. Sci. Pharm., 2012, Vol. 80, pp.837-865 doi: 10.3797/scipharm.1208-07

10. Kovalenko S. I., Nosulenko I. S., Voskoboynik A. Yu., Berest G. G., Antypenko L. M., Antipenko A. N., Katsev A. M. Med. Chem. Res., 2013, Vol. 22(6), pp.2610-2632. doi: 10.1007/s00044-012-0257-x

11. Vulfson N. S., Zaikin V. G., Mikaia A. I. Mass-spektroskopia organicheskih soedinenii (Mass-spectrometry of organic compounds). Moskow, 312 p.

12. Bagrii E. I. Osobenosti stroenia i svoystv adamantanov (The characteristics of structure and properties of adamantanes) Moskow, 1989, 264 p.

13. Breitmaier E. Structure Elucidation by NMR In Organic Chemistry: A Practical Guide, Wiley &Sons, Ltd, 2002, 258 p.


15. Sidwell R. W., Smee D. F. In vitro and in vivo assay systems for study of influenza virus inhibitors. Antiviral Research, 2000, Vol. 48, pp.1-16 doi: 10.1016/S0166-3542(00)00125-X

16. Berest G. G., Voskoboynik A. Y., Kovalenko S. I., Antypenko A. M., Nosulenko I. S., Katsev A. M., Shandrovskaya A. S. Eur. J. Med. Chem., 2011, Vol. 46, pp.6066-6074 doi: 10.1016/j.ejmech.2011.10.022

17. Berest G. G., Voskoboynik O. Yu., Nosulenko I. S., Rak I. E., Sinyak R. S., Kovalenko S. I. Klinicheskaya farmaciia, farmakoterapiia i medichna standartizaciia. – Clinical pharmacy, pharmacotherapy and medical standardization, 2011, Vol. 1-2(10-11), pp.197-205.


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