8-(Methyl sulfo nyl)-2,6-dihydroimidazo[1,2-c]pyrimidine-5- (3H)-ones — new heterocyclic derivatives of sulfones with antiviral activity

Authors

  • R.M. Solomyannyi V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kiev,
  • V.S. Brovarets V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kiev,
  • O.V. Shablykina V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kiev,
  • V.S. Moskvina V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kiev,
  • V.P. Khilya Taras Shevchenko National University of Kiev

DOI:

https://doi.org/10.15407/dopovidi2019.05.075

Keywords:

2-c]pyrimidine- 5(3H)-one, 3-amino-2-(methylsulfonyl)acrylonitrile, 6-dihydroimidazo[1, 8-(methylsulfonyl)-2, antiviral activity, heterocyclylization

Abstract

By the interaction of 3-(R-amino)-2-(methylsulfonyl)acrylonitrile and 1-isocyanate-2-chloroethane, new sulfonе analogues of cytosine, 8-(methylsulfonyl)-6-R-2,6-dihydroimidazo[1,2-c]pyrimidine-5(3H)-ones, are synthesized. The antiviral activity of 8-(methylsulfonyl)-6-benzyl-2,6-dihydroimidazo[1,2-c]pyrimidine-5(3H)-one has been proven.

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References

Straub, A., Stasch, J. P., Alonso-Alija, C., Benet-Buchholz, J., Ducke, B., Feurer, A. & Fürstner, C. (2001). NOIndependent stimulators of soluble guanylate cyclase. Bioorg. Med. Chem. Lett., 11, Iss. 6, pp. 781-784. doi: https://doi.org/10.1016/S0960-894X(01)00073-7

Semenov, A. A., Kartsev, V. G. (2009). Foundations of the chemistry of natural compounds. Vol. 2. Мoscow: ICSPF (in Russian).

Brovarets, V., Solomyannyi, R., Slivchuk, S., Zhirnov, V., Rusanov, E., Smee, D. & Choi, J. (2018). In vitro activity of the novel pyrimidines and their condensed derivatives against poliovirus. Curr. Bioact. Compd., 14, Iss. 9, pp. 1-9. doi: https://doi.org/10.2174/1573407214666180720120509

Kifli, N., De Clercq, E., Balzarini, J. & Simons, C. (2004). Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: synthesis and antiviral evaluation. Bioorg. Med. Chem., 12, Iss. 15, pp. 4245-4252. doi: https://doi.org/10.1016/j.bmc.2004.05.017

Ermolin, S. V., Kost, A. A., Ivanov, M. V. & Nagradova, N. K. (1978). Ethylene derivatives of cytosine as fluorescent probes in the study of D-glyceraldehyde-3-phosphate dehydrogenase. Dokl. AN SSSR, 238, Iss. 1, pp. 245-248 (in Russian).

Zhang, W., Rieger, R., Iden, C. & Johnson, F. (1995). Synthesis of 3,N4-etheno, 3,N4-ethano, and 3-(2-hydroxyethyl) derivatives of 2′-deoxycytidine and their incorporation into oligomeric DNA. Chem. Res. Toxicol., 8, Iss. 1, pp. 148-156. doi: https://doi.org/10.1021/tx00043a020

Slivchuk, S. R., Brovarets, V. S. & Drach, B.S. (2006). Convenient synthesis of uracil and cytosine derivatives with arylsulfonyl residues near the center of C5. Dopov. Nac. akad. nauk Ukr., No. 3, pp. 146-152 (in Ukrainian).

Pigošová, J., Gatial, A., Milata, V., Černuchová, P., Prónayová, N., Liptaj, T. & Matějka, P. (2005). The isomers and conformers of some push-pull-enamines studied by vibrational and NMR spectroscopy and by ab initio calculations. J. Mol. Struct., 744, pp. 315-324. doi: https://doi.org/10.1016/j.molstruc.2004.10.053

Lunt, E., Newton, C. G., Smith, C., Stevens, G. P., Stevens, M. F. G., Straw, C. G., Walsh, R. J. A., Warren, P. J., Fizames, C., Lavelle, F., Langdon, S. P. & Vickers, L. M. (1987). Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyra zolo [5,1-d]-1,2,3,5-tetrazinones. J. Med. Chem., 30, Iss. 2, pp. 357-366. doi: https://doi.org/10.1021/jm00385a018

Published

21.04.2024

How to Cite

Solomyannyi, R., Brovarets, V., Shablykina , O., Moskvina, V., & Khilya, V. (2024). 8-(Methyl sulfo nyl)-2,6-dihydroimidazo[1,2-c]pyrimidine-5- (3H)-ones — new heterocyclic derivatives of sulfones with antiviral activity . Reports of the National Academy of Sciences of Ukraine, (5), 75–81. https://doi.org/10.15407/dopovidi2019.05.075

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