Synthesis and antiviral activity of new dimers of 1,2,3-triazolyl pyrimidine nucleoside analogues
- Authors: Andreeva O.V.1, Saifina L.F.1, Shulaeva M.M.1, Belenok M.G.1, Zarubaev V.V.2, Slita A.V.2, Volobueva A.S.2, Semenov V.E.1, Kataev V.E.1
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Affiliations:
- Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
- Pasteur Institute of Epidemiology and Microbiology
- Issue: Vol 60, No 4 (2024)
- Pages: 428-441
- Section: Articles
- URL: https://aspvestnik.ru/0514-7492/article/view/672154
- DOI: https://doi.org/10.31857/S0514749224040036
- EDN: https://elibrary.ru/RZMGOA
- ID: 672154
Cite item
Abstract
A series of new dimers of pyrimidine nucleoside analogues have been synthesized. The dimers are composed of two uracil or thymine fragments linked at N3 through a polymethylene bridge and bearing a β-D-ribofuranose residue linked to N1 of the nucleobase through a 1,2,3-triazolylalkyl spacer. Biological screening revealed that some of the synthesized dimers are active against influenza A (H1N1) virus and coxsackievirus B3 with IC50 values of 13 and 4.5 μM, respectively.
About the authors
O. V. Andreeva
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Author for correspondence.
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-5518-8395
Russian Federation, Arbuzov str., 8, Kazan, 420088
L. F. Saifina
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-7504-1331
Russian Federation, Arbuzov str., 8, Kazan, 420088
M. M. Shulaeva
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-6014-0177
Russian Federation, Arbuzov str., 8, Kazan, 420088
M. G. Belenok
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Email: andreeva@iopc.ru
ORCID iD: 0000-0002-0906-8226
Russian Federation, Arbuzov str., 8, Kazan, 420088
V. V. Zarubaev
Pasteur Institute of Epidemiology and Microbiology
Email: andreeva@iopc.ru
ORCID iD: 0000-0002-5224-3771
Russian Federation, Mira Str.,14, Saint Petersburg, 197101
A. V. Slita
Pasteur Institute of Epidemiology and Microbiology
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-8229-0715
Russian Federation, Mira Str.,14, Saint Petersburg, 197101
A. S. Volobueva
Pasteur Institute of Epidemiology and Microbiology
Email: andreeva@iopc.ru
ORCID iD: 0000-0003-0839-852X
Russian Federation, Mira Str.,14, Saint Petersburg, 197101
V. E. Semenov
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-8350-2433
Russian Federation, Arbuzov str., 8, Kazan, 420088
V. E. Kataev
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science
Email: andreeva@iopc.ru
ORCID iD: 0000-0002-2767-2793
Russian Federation, Arbuzov str., 8, Kazan, 420088
References
- Watson J.D., Crick F. H.C. Nature, 1953, 171, 737‒738. doi: 10.1038/171737a0
- Hoogsteen K. Acta Crystallogr. 1963, 16, 907‒916. doi: 10.1107/S0365110X63002437
- Browne D.T, Eisinger J., Leonard N. J. J. Am. Chem. Soc. 1968, 90, 7302‒7323. doi: 10.1021/ja01028a023
- Leonard N.L., McCredie R.S., Logue M. W., Cundall R. L. J. Am. Chem. Soc. 1973, 95, 2320‒2324. doi: 10.1021/ja00788a036
- Itahara T. Bull. Chem. Soc. Jpn. 1997, 70, 2239‒2247. doi: 10.1246/bcsj.70.2239
- Semenov V.E., Akamsin V. D., Reznik V. S. Russ. J. Gen. Chem. 2001, 71, 1088‒1090. doi: 10.1023/A:1013161906788
- Raza A., Dreis C. D., Vince R. Bioorg. Med. Chem. Lett. 2013, 23, 620‒623. doi: 10.1016/j.bmcl.2012.12.023
- Aparici-Espert I., Garcia-Lainez G., Andreu I., Miranda M. A., Lhiaubet-Vallet V. ACS Chem. Biol. 2018, 13, 542‒547. doi: 10.1021/acschembio.7b01097
- Alzueta O.R., Consuelo Cuquerella M., Miranda M. A. J. Org. Chem. 2019, 84, 13329‒13335. doi: 10.1021/acs.joc.9b01423
- Leonard N.J., Cundall R. L. J. Am. Chem. Soc. 1974, 96, 5904‒5910. doi: 10.1021/ja00825a030
- Kinoshita T., Odawara S., Fukumura K., Furukawa S. J. Heterocycl. Chem. 1985, 22, 1573‒1576. doi: 10.1002/jhet.5570220621
- Diogo H.P., Dias A. R., Dhalla A., Minas da Piedade M. E., Begley T. P. J. Org. Chem. 1991, 56, 7340‒7341. doi: 10.1021/jo00026a029
- Itahara T., Imamura K. Bull. Chem. Soc. Jpn. 1994, 67, 203–209. doi: 10.1246/bcsj.67.203
- Alqarni Y., Bell T. D.M., Tabor R. F., Saito K. J. Org. Chem. 2019, 84, 8596‒8601. doi: 10.1021/acs.joc.9b00913
- Zoorob H.H., Ismail M.A J. Heterocycl. Chem. 2001, 38, 359‒363. doi: 10.1002/ejoc.201001581
- Das S., Thakur A. J. Eur. J. Org. Chem. 2011, 12, 2301‒2308. doi: 10.1002/ejoc.201001581
- Semenov V.E., Akamsin V. D., Reznik V. S., Chernova A. V., Dorozhkina G. M., Efremov Y. Ya., Nafikova A. A. Tetrahedron Lett. 2002, 43, 9683–9686. doi: 10.1016/S0040–4039(02)02424–3
- Zemlicka J., Owens J. J. Org. Chem. 1977, 42, 517‒523. doi: 10.1021/jo00423a026
- Ogilvie K.K., Beaucage S. L., Gillen M. F. Tetrahedron Lett. 1978, 19, 1663‒1666. doi: 10.1016/S0040–4039(01)94634–9
- Wilds C.J., Noronha A. M., Robidoux S., Miller P. S., J. Am. Chem. Soc. 2004, 126, 9257‒9265. doi: 10.1021/ja0498540
- Ariza X., Farras J., Serra C., Vilarrasa J. J. Org. Chem. 1997, 62, 1547‒1549. doi: 10.1021/jo9615514
- Ogilvie K.K., Beaucage S. L., Gillen M. F., Entwistle D., Quilliam M. Nucleic Acids Res. 1979, 6, 1695‒1708. doi: 10.1093/nar/6.4.1695
- Tanabe K., Sugiura M., Ito T., Nishimoto S. Bioorg. Med. Chem. 2012, 20, 5164‒5168. doi: 10.1016/j.bmc.2012.07.008
- Kaz’mina E.M., Fedorov I. I., Bezchinskii Ya.E., Kiseleva N. V., Novikov N. A., Galegov G. G., Arzamastsev A. P. Pharm. Chem. J. 1989, 23, 830‒836. doi: 10.1007/BF00764813
- Li G.-R., Liu J., Pan Q., Song Z.-B., Luo F.-L., Wang S.-R., Zhang X.-L., Zhou X. Chem. Biodivers. 2009, 6, 2200‒2208. doi: 10.1002/cbdv.200800281
- Mainkar P.S., Sridhar C., Sudhakar A., Chandrasekhar S. Helv. Chim. Acta, 2013, 96, 99‒108. doi: 10.1002/hlca.201200060
- Murata S., Mizumura Y., Hino K., Ueno Y., Ichikawa S., Matsuda A. J. Am. Chem. Soc. 2007, 129, 10300‒10301. doi: 10.1021/ja071335k
- Sun G., Noronha A., Wilds C. Tetrahedron, 2012, 68, 7787–7793. doi: 10.1016/j.tet.2012.07.043
- Семенов В.Э., Николаев А. Е., Крылова Е. С., Шарафутдинова Д. Р., Резник В. С. ЖОрХ. 2012, 48, 584–589. [Semenov V. E., Nikolaev A. E., Krylova E. S., Sharafutdinova D. R., Reznik V. S. Russ. J. Org. Chem. 2012, 48, 582–587.] doi: 10.1134/S1070428012040203
- Andreeva O.V., Belenok M. G., Saifina L. F., Shulaeva M. M., Dobrynin A. B., Sharipova R. R., Voloshina A. D., Saifina A. F., Gubaidullin A. T., Khairutdinov B. I., Zuev Yu.F., Semenov V. E., Kataev V. E. Tetrahedron Lett. 2019, 60, 151276. doi: 10.1016/j.tetlet.2019.151276
- Шарипова Р.Р., Беленок М. Г., Семенов В. Э., Катаев В. Е. ЖОрХ. 2020, 56, 148–152. [Sharipova R.R, Saifina L. F., Belenok M. G., Semenov V. E., Kataev V. E. Russ. J. Org. Chem. 2020, 56, 181‒184.] doi: 10.1134/S1070428020010285
- Strobykina I. Yu., Andreeva O. V., Belenok M. G., Semenova M. N., Semenov V. V., Chuprov-Netochin R.N., Sapunova A. S., Voloshina A. D., Dobrynin A. B., Semenov V. E., Kataev V. E. Med. Chem. Res. 2020, 29, 2203‒2217. doi: 10.1007/s00044–020–02629-x
- Andreeva O.V., Garifullin B. F., Zarubaev V. V., Slita A. V., Yesaulkova I. L., Saifina L. F., Shulaeva M. M., Belenok M. G., Semenov V. E., ·Kataev V. E. Mol. Divers. 2021, 25, 473‒490. doi: 10.1007/s11030–020–10141-y
- Андреева О.В., Сайфина Л. Ф., Беленок М. Г., Семенов В. Э., Катаев В. Е. ЖОрХ. 2021, 57, 291–296. [Andreeva O. V., Saifina L. F., Belenok M. G., Semenov V. E., Kataev V. E. Russ. J. Org. Chem. 2021, 57, 292‒296.] doi: 10.1134/S1070428021020226
- Семенов В.Э., Волошина А. Д., Кулик Н. В., Стробыкина А. С., Гиниятуллин Р. Х., Сайфина Л. Ф., Николаев А. Е., Крылова Е. С., Зобов В. В., Резник В. С. Изв. АН. Сер. хим. 2015, 12, 2885‒2896. [Semenov V. E., Voloshina A. D., Kulik N. V., Strobykina A. S., Giniyatullin R. K., Saifina L. F., Nikolaev A. E., Krylova E. S., Zobov V. V., Reznik V. S. Russ. Chem. Bull. Intern. Ed. 2015, 64, 2885‒2896.] doi: 10.1007/s11172–015–1243–5
- Semenov V.E., Zueva I. V., Lushchekina S. V., Suleimanov E. G., Gubaidullina L. M., Shulaeva M. M., Lenina O. A., Petrov K. A. Molecules. 2022, 27, 7855. doi: 10.3390/molecules27227855
- Saifina L.F., Abdalla M., Gubaidullina L. M., Zueva I. V., Eltayb W. A., El-Arabey A.A., Kharlamova A. D., Lenina O. A., Semenov V. E., Petrov K. A. Eur. J. Med. Chem. 2023, 246, 114949. doi: 10.1016/j.ejmech.2022.114949
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