SYNTHESIS OF 1-[ω-(BROMOPHENOXY)ALKYL]-3-NAPHTHALENYLMETHYL DERIVATIVES OF URACIL AND THEIR ANALOGUES AS PROBABLE INHIBITORS OF HUMAN CYTOMEGALOVIRUS REPLICATION

M. P. Paramonova; Парамонова М. П.; E. S. Gureeva; Гуреева Е. С.; A. A. Ozerov; Озеров А. А.; R. Snoeck; Snoeck R.; G. Andrei; Andrei G.; D. A. Aleksandrov; Александров Д. А.; A. L. Khandazhinskaya; Хандажинская А. Л.; M. S. Novikov; Новиков М. С.; S. N. Kochetkov; Кочетков С. Н.

doi:10.31857/S2686738922700093

SYNTHESIS OF 1-[ω-(BROMOPHENOXY)ALKYL]-3-NAPHTHALENYLMETHYL DERIVATIVES OF URACIL AND THEIR ANALOGUES AS PROBABLE INHIBITORS OF HUMAN CYTOMEGALOVIRUS REPLICATION

Authors: Paramonova M.P.¹, Gureeva E.S.¹, Ozerov A.A.¹, Snoeck R.², Andrei G.², Aleksandrov D.A.³, Khandazhinskaya A.L.⁴, Novikov M.S.¹, Kochetkov S.N.⁴
Affiliations:
1. Volgograd State Medical University
2. Rega Institute for Medical Research, KU Leuven
3. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences
4. Institute of Molecular Biology, Russian Academy of Sciences, V.A. Engelhardt RAS
Issue: Vol 509, No 1 (2023)
Pages: 170-176
Section: Articles
URL: https://ruspoj.com/2686-7389/article/view/651131
DOI: https://doi.org/10.31857/S2686738922700093
EDN: https://elibrary.ru/NAUWWD
ID: 651131

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription or Fee Access

Abstract

A synthesis of a new series of 1-[ω-(bromophenoxy)alkyl]-uracil derivatives containing in position 3 naphthalen-1-yl-, naphthalen-2-yl-, 1-bromonaphthalen-2-ylmethyl, benzyl, and anthracene 9-methyl fragment was carried out. The antiviral properties of the synthesized compounds were studied against human cytomegalovirus. It was found that the compound, which has in its composition a bridge consisting of five methylene groups, has a high anti-cytomegalovirus activity in vitro.

Keywords

uracil derivatives, synthesis, antiviral activity, human cytomegalovirus

About the authors

M. P. Paramonova

Volgograd State Medical University

Email: snk1952@gmail.com
Russian, Volgograd

E. S. Gureeva

Volgograd State Medical University

Email: snk1952@gmail.com
Russian, Volgograd

A. A. Ozerov

Volgograd State Medical University

Email: snk1952@gmail.com
Russian, Volgograd

R. Snoeck

Rega Institute for Medical Research, KU Leuven

Email: snk1952@gmail.com
Belgium, B-3000, Leuven, Herestraat 49 bus 1043

G. Andrei

Rega Institute for Medical Research, KU Leuven

Email: snk1952@gmail.com
Belgium, B-3000, Leuven, Herestraat 49 bus 1043

D. A. Aleksandrov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences

Email: snk1952@gmail.com
Russian, Moscow

A. L. Khandazhinskaya

Institute of Molecular Biology, Russian Academy of Sciences, V.A. Engelhardt RAS

Author for correspondence.
Email: khandazhinskaya@bk.ru
Russian, Moscow

M. S. Novikov

Volgograd State Medical University

Email: snk1952@gmail.com
Russian, Volgograd

S. N. Kochetkov

Institute of Molecular Biology, Russian Academy of Sciences, V.A. Engelhardt RAS

Author for correspondence.
Email: snk1952@gmail.com
Russian, Moscow

References

Rodríguez-Goncer I., Fernández-Ruiz M., Aguado J.M. // Expert Rev. Anti. Infect. Ther. 2020. V. 18. P. 113–125.
Karrer U., Mekker A., Wanke K., Tchang V., Haeberli L. // Exp. Gerontol. 2009. V. 44. P. 689–694.
Jentzer A., Veyrard P., Roblin X., Saint-Sardos P., Rochereau N., Paul S., Bourlet T., Pozzetto B., Pillet S. // Microorganisms. 2020. V. 8. P. 1078.
Richardson A.K., Walker L.C., Cox B., Rollag H., Robin-son B.A., Morrin H., Pearson J.F., Potter J.D., Paterson M., Surcel H.M., Pukkala E., Currie M.J. // Clin. Transl. Oncol. 2020. V. 22. P. 585–602.
Lv Y.L., Han F.F., An Z.L., Jia Y., Xuan L.L., Gong L.L., Zhang W., Ren L.L., Yang S., Liu H., Liu L.H. // Intervirology. 2020. V. 63. P. 10–16.
Plotkin S.A., Boppana S.B. // Vaccine. 2019. V. 37. P. 7437–7442.
Permar S.R., Schleiss M.R., Plotkin S.A. // J. Virol. 2018. V. 92. P. e00030-18.
Kotton C.N. // Curr Opin Organ Transplant. 2019. V. 24. P. 469–475.
Sellar R.S., Peggs K.S. // Expert Opin. Biol. Ther. 2012. V. 12. P. 1161–1172.
Faure E., Galperine T., Cannesson O., Alain S., Gnemmi V., Goeminne C., Dewilde A., Béné J., Lasri M., Lessore de Sainte Foy C., Lionet A. // Medicine. 2016. V. 95. P. e5226.
Tan B.H. // Options Infect. Dis. 2014. V. 6. P. 256–270.
El Helou G., Razonable R.R. // Infect. Drug Resist. 2019. V. 12. P. 1481–1491.
Papanicolaou G.A., Silveira F.P., Langston A.A., Pereira M.R., Avery R.K., Uknis M., Wijatyk A., Wu J., Boeckh M., Marty F.M., Villano S. // Clin. Infect. Dis. 2019. V. 68. P. 1255–1264.
Piret J., Boivin G. // Antiviral Res. 2019. V. 163. P. 91–105.
Novikov M.S., Babkov D.A., Paramonova M.P., Khandazhinskaya A.L., Ozerov A.A., Chizhov A.O., Andrei G., Snoeck R., Balzarini J., Seley-Radtke K.L. // Bioorg. Med. Chem. 2013. V. 21. P. 4151–4157.
Babkov D.A., Khandazhinskaya A.L., Chizhov A.O., Andrei G., Snoeck R., Seley-Radtke K.L., Novikov M.S. // Bioorg. Med. Chem. 2015. V. 23. P. 7035–7044.
Maruyama T., Kozai S., Yamasaki T., Witvrouw M., Pannecouque C., Balzarini J., Snoeck R., Andrei G., De Clercq E. // Antivir. Chem. Chemother. 2003. V. 14. P. 271–279.
Maruyama T., Demizu Y., Kozai S., Witvrouw M., Pannecouque C., Balzarini J., Snoecks R., Andrei G., De Clercq E. // Nucleosides Nucleotides Nucleic Acids. 2007. V. 26. P. 1553–1558.
Novikov M.S., Valuev-Elliston V.T., Babkov D.A., Paramonova M.P., Ivanov A.V., Gavryushov S.A., Khandazhinskaya A.L., Kochetkov S.N., Pannecouque C., Andrei G., Snoeck R., Balzarini J., Seley-Radtke K.L. // Bioorg. Med. Chem. 2013. V. 21. P. 1150–1158.
Paramonova M.P., Khandazhinskaya A.L., Ozerov A.A., Kochetkov S.N., Snoeck R., Andrei G., Novikov M.S. // Acta Naturae. 2020. V. 12. P. 134–139.
Paramonova M.P., Snoeck R., Andrei G., Khandazhinskaya A.L., Novikov M.S. // Mendeleev Commun. 2020. V. 30. P. 602–603.
Snoeck R., Sakuma T., De Clercq E., Rosenberg I., Holy A. // Antimicrob. Agents Chemother. 1988. V. 32. P. 1839–1844.
Baker B.R., Kelley J.L. // J. Med. Chem. 1970. V. 13. P. 458–461.