Synthesis and antiviral activity of new dimers of 1,2,3-triazolyl pyrimidine nucleoside analogues

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

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.

Авторлар туралы

O. Andreeva

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science

Хат алмасуға жауапты Автор.
Email: andreeva@iopc.ru
ORCID iD: 0000-0001-5518-8395
Ресей, Arbuzov str., 8, Kazan, 420088

L. 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
Ресей, Arbuzov str., 8, Kazan, 420088

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
Ресей, Arbuzov str., 8, Kazan, 420088

M. 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
Ресей, Arbuzov str., 8, Kazan, 420088

V. Zarubaev

Pasteur Institute of Epidemiology and Microbiology

Email: andreeva@iopc.ru
ORCID iD: 0000-0002-5224-3771
Ресей, Mira Str.,14, Saint Petersburg, 197101

A. Slita

Pasteur Institute of Epidemiology and Microbiology

Email: andreeva@iopc.ru
ORCID iD: 0000-0001-8229-0715
Ресей, Mira Str.,14, Saint Petersburg, 197101

A. Volobueva

Pasteur Institute of Epidemiology and Microbiology

Email: andreeva@iopc.ru
ORCID iD: 0000-0003-0839-852X
Ресей, Mira Str.,14, Saint Petersburg, 197101

V. 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
Ресей, Arbuzov str., 8, Kazan, 420088

V. 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
Ресей, Arbuzov str., 8, Kazan, 420088

Әдебиет тізімі

  1. Watson J.D., Crick F. H.C. Nature, 1953, 171, 737‒738. doi: 10.1038/171737a0
  2. Hoogsteen K. Acta Crystallogr. 1963, 16, 907‒916. doi: 10.1107/S0365110X63002437
  3. Browne D.T, Eisinger J., Leonard N. J. J. Am. Chem. Soc. 1968, 90, 7302‒7323. doi: 10.1021/ja01028a023
  4. Leonard N.L., McCredie R.S., Logue M. W., Cundall R. L. J. Am. Chem. Soc. 1973, 95, 2320‒2324. doi: 10.1021/ja00788a036
  5. Itahara T. Bull. Chem. Soc. Jpn. 1997, 70, 2239‒2247. doi: 10.1246/bcsj.70.2239
  6. Semenov V.E., Akamsin V. D., Reznik V. S. Russ. J. Gen. Chem. 2001, 71, 1088‒1090. doi: 10.1023/A:1013161906788
  7. Raza A., Dreis C. D., Vince R. Bioorg. Med. Chem. Lett. 2013, 23, 620‒623. doi: 10.1016/j.bmcl.2012.12.023
  8. 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
  9. Alzueta O.R., Consuelo Cuquerella M., Miranda M. A. J. Org. Chem. 2019, 84, 13329‒13335. doi: 10.1021/acs.joc.9b01423
  10. Leonard N.J., Cundall R. L. J. Am. Chem. Soc. 1974, 96, 5904‒5910. doi: 10.1021/ja00825a030
  11. Kinoshita T., Odawara S., Fukumura K., Furukawa S. J. Heterocycl. Chem. 1985, 22, 1573‒1576. doi: 10.1002/jhet.5570220621
  12. 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
  13. Itahara T., Imamura K. Bull. Chem. Soc. Jpn. 1994, 67, 203–209. doi: 10.1246/bcsj.67.203
  14. Alqarni Y., Bell T. D.M., Tabor R. F., Saito K. J. Org. Chem. 2019, 84, 8596‒8601. doi: 10.1021/acs.joc.9b00913
  15. Zoorob H.H., Ismail M.A J. Heterocycl. Chem. 2001, 38, 359‒363. doi: 10.1002/ejoc.201001581
  16. Das S., Thakur A. J. Eur. J. Org. Chem. 2011, 12, 2301‒2308. doi: 10.1002/ejoc.201001581
  17. 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
  18. Zemlicka J., Owens J. J. Org. Chem. 1977, 42, 517‒523. doi: 10.1021/jo00423a026
  19. Ogilvie K.K., Beaucage S. L., Gillen M. F. Tetrahedron Lett. 1978, 19, 1663‒1666. doi: 10.1016/S0040–4039(01)94634–9
  20. Wilds C.J., Noronha A. M., Robidoux S., Miller P. S., J. Am. Chem. Soc. 2004, 126, 9257‒9265. doi: 10.1021/ja0498540
  21. Ariza X., Farras J., Serra C., Vilarrasa J. J. Org. Chem. 1997, 62, 1547‒1549. doi: 10.1021/jo9615514
  22. 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
  23. Tanabe K., Sugiura M., Ito T., Nishimoto S. Bioorg. Med. Chem. 2012, 20, 5164‒5168. doi: 10.1016/j.bmc.2012.07.008
  24. 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
  25. 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
  26. Mainkar P.S., Sridhar C., Sudhakar A., Chandrasekhar S. Helv. Chim. Acta, 2013, 96, 99‒108. doi: 10.1002/hlca.201200060
  27. Murata S., Mizumura Y., Hino K., Ueno Y., Ichikawa S., Matsuda A. J. Am. Chem. Soc. 2007, 129, 10300‒10301. doi: 10.1021/ja071335k
  28. Sun G., Noronha A., Wilds C. Tetrahedron, 2012, 68, 7787–7793. doi: 10.1016/j.tet.2012.07.043
  29. 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
  30. 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
  31. 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
  32. 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
  33. 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
  34. 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
  35. 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
  36. 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
  37. 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

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2024