Title | 8-(Methyl sulfo nyl)-2,6-dihydroimidazo[1,2-c]pyrimidine-5- (3H)-ones — new heterocyclic derivatives of sulfones with antiviral activity |
Publication Type | Journal Article |
Year of Publication | 2019 |
Authors | Solomyannyi, RM, Brovarets, VS, Shablykina, OV, Moskvina, VS, Khilya, VP |
Abbreviated Key Title | Dopov. Nac. akad. nauk Ukr. |
DOI | 10.15407/dopovidi2019.05.075 |
Issue | 5 |
Section | Chemistry |
Pagination | 75-81 |
Date Published | 05/2019 |
Language | Ukrainian |
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. |
Keywords | 2-c]pyrimidine- 5(3H)-one, 3-amino-2-(methylsulfonyl)acrylonitrile, 6-dihydroimidazo[1, 8-(methylsulfonyl)-2, antiviral activity, heterocyclylization |
1. 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
2. Semenov, A. A., Kartsev, V. G. (2009). Foundations of the chemistry of natural compounds. Vol. 2. Мoscow: ICSPF (in Russian).
3. 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
4. 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
5. 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).
6. 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
7. 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).
8. 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
9. 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