Synthesis, spectral, electrochemical properties, antioxidant and antiviral activity of new 2-[5-phenyl-6-methyl-3-aryl/getaryl-5,6-dihydro-4h-[1,2,4,5]tetrazine-1-yl]-benzothiazoles

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Abstract

New 2-[5-aryl-6-methyl-3-aryl/getaryl-5,6-dihydro-4H-[1,2,4,5]tetrazine-1-yl]-benzothiazole has been synthesized from the corresponding formazanes by alkylation and subsequent cyclization of N-alkyl derivatives. The products are characterized by 1H, 13C NMR, IR, spectroscopy, mass spectrometry and X-ray diffraction analysis. The electrochemical properties, antioxidant and antiviral activity of the obtained benzothiazoles were studied.

About the authors

T. G. Fedorchenko

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108

G. N. Lipunova

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108

A. S. Volobueva

St. Petersburg Pasteur Institute

Email: flumd@mail.ru
Russian Federation, 197101, St. Petersburg, Mira str., 14

V. V. Zarubaev

St. Petersburg Pasteur Institute

Email: flumd@mail.ru
Russian Federation, 197101, St. Petersburg, Mira str., 14

M. S. Valova

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108

A. V. Shchepochkin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal named after the first President of Russia B. N. Yeltsin

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108; ul. Mira, 19, Yekaterinburg, 620002

M. A. Averkov

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal named after the first President of Russia B. N. Yeltsin

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108; ul. Mira, 19, Yekaterinburg, 620002

V. N. Tungusov

Ural Federal named after the first President of Russia B. N. Yeltsin

Email: flumd@mail.ru
Russian Federation, ul. Mira, 19, Yekaterinburg, 620002

P. A. Slepukhin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal named after the first President of Russia B. N. Yeltsin

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108; ul. Mira, 19, Yekaterinburg, 620002

O. N. Chupakhin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal named after the first President of Russia B. N. Yeltsin

Email: flumd@mail.ru
Russian Federation, ul. S. Kovalevskoi, 22/20, Yekaterinburg 620108; ul. Mira, 19, Yekaterinburg, 620002

References

  1. Valko M., Leibfritz D., Moncol J., Cronin M.T.D., Mazur M., Telser J. Int. J. Biochem. Cell. Biol. 2007, 39, 44–84. doi: 10.1016/j.biocel.2006.07.001
  2. Ai Pham-Huy L., He H., Pham-Huyc C. Int. J. Biomed. Sci. 2008, 4, 89–96. http://www.ijbs.org/User/All-by-date.aspx
  3. Yuting S., De J., Ziwei Zh., Yuehong Zh., Yuqing Zh., Xiaomin K., Linlin J., Xiaolin T., Fengmei L. Chinese Med. 2023, 18, 3. doi.org/10.1186/s13020-022-00700-w
  4. Saixian Shi, Ye Chen, Zhijian Luo, Guojun Nie, Yan Dai Cell Commun. Signaling. 2023, 21, 61. doi: 10.1186/s12964-023-01077-5
  5. Hussain H.H., Babic G., Durst T., Wright J., Flueraru M., Chichirau A., Chepelev L.L.J. Org. Chem. 2003, 68, 7023–7032. doi: 10.1021/jo0301090
  6. Didier A.J., Stiene J., Fang L., Watkins D., Dworkin L.D., Creeden J.F. Antioxidants. 2023, 12, 632. doi: 10.3390/antiox12030632
  7. Rago V., Di Agostino S. Antioxidants. 2023, 12, 289. doi: 10.3390/antiox12020289
  8. Вестман Я. Пат. 2798107 (2019). РФ.Б.И. 2022, 31.
  9. Sarbu C., Casoni D., Cent. Eur. J. Chem. 2013, 11, 679–688. doi: 10.2478/s11532-013-0210-y
  10. Николаева Н.С., Солдатова Ю.В., смолина А.В., Аксиненко А.Ю., Соколов В.Б., Кинзирский А.С., Котельникова Р.А., Штолко В.Н., Котельников А.И. Изв. АН. Сер. хим. 2017, 66, 870–874. [Nikolaeva N.S., Soldatova Yu.V., Smolina A.V., Aksinenko A.Yu., Sokolov V.B., Kinzirsky A.S., Kotel’nikova R.A., Shtolko V.N., Kotel’nikov A.I. Russ. Chem. Bull. 2017, 66, 870–874.] doi: 10.1007/s11172-017-1821-9
  11. Милаева Е.З., Шпаковский Д.Б., Маклакова И.А., Зуфанов К.А., Неганова М.Е., Шевцова Е.Ф., Чураков А.В., Бабкова В.А., Бабков Д.А., Косолапов В.А., Спасов А.А. Изв. АН. Сер. хим. 2018, 67, 2025–2034. [Milaeva E.R., Shpakovsky D.B., Maklakova I.A., Rufanov K.A., Neganova M.E., Shevtsova E.F., Churakov A.V., Babkova V.A., Babkov D.A., Kosolapov V.A., Spasov A.A. Russ. Chem. Bull. 2018, 67, 2025–2034.] doi: 10.1007/s11172-018-2324-z
  12. El-Mekabaty A., El-Shora H.M. Chem. Heterocycl. Compd. 2018, 54, 618–624. doi: 10.1007/s10593-018-2317-8
  13. Makhaeva G.F., Lushchekina S.V., Boltneva N.P., Serebryakova O.G., Rudakova E.V., Ustyugov A.A., Bachurin S.O., Shchepochkin A.V., Chupakhin O.N., Charushin V.N., Richardson R.J. Bioorg. Med. Chem. 2017, 25, 5981–5994. doi: 10.1016/j.bmc.2017.09.028
  14. Федорченко Т.Г., Липунова Г.Н., Щепочкин А.В., Валова М.С., Цмокалюк А.Н., Слепухин П.А., Чупахин О.Н., ЖОрХ. 2020, 56, 52–64. [T.G. Fedorchenko, G.N. Lipunova, A.V. Shchepochkin, M.S. Valova, P.A. Slepukhin, O.N. Chupakhin, A.N. Tsmokalyuk, Russ. J. Org. Chem. (Engl. Transl.), 2020, 56, 38–48.] doi: 10.1134/S1070428020010078
  15. Волобуева А.С., Федорченко Т.Г., Зарубаев В.В. Первая всероссийская школа по медицинской химии для молодых ученых, 4-9 июля 2021 г., Сборник тез. докл., Новосибирск, 2021, 65
  16. Федорченко Т.Г., Волобуева А.С., Тунгусов В.Н., Зарубаев В.В., Липунова Г.Н., Чупахин О.Н. Пат. 2783659 (2022) РФ.Б.И. 2022, 32.
  17. Волобуева А.С., Зарубаев В.В., Федорченко Т.Г., Липунова Г.Н., Тунгусов В.Н., Чупахин О.Н. Инфекция и иммунитет. 2023, 13, 107–118. [Volobueva A.S., Zarubaev V.V., Fedorchenko T.G., Lipunova G.N., Tungusov V.N., Chupakhin O.N. Russ. J. Infect.Immunity, 2023, 13, 107–118.] doi.org/10.15789/2220-7619-VAL-2065
  18. Петунин П.В., Плотников Е.В., Воткина Д.Е., Постников П.С., Трусова М.Е. Пат. 2771237 (2021) РФ.Б.И. 2022, 13.
  19. Votkina D.E., Plotnikov E.V., Petunin P.V., Berdinskaya E.S., Tretyakova M.S., Audran G. Marque S.R.A., Postnikov P.S. Mol. Pharmaceut. 2022, 19, 354–357. doi: 10.1021/acs.molpharmaceut.1c00780
  20. Sharma O.P., Bhat T.K., Food Chem. 2009, 113, 1202-1205. doi: 10.1016/j.foodchem.2008.08.008
  21. Леонова Г.Н., Майстровская О.С., Лубова В.А. Антибиотики и Химиотерапия. 2020, 65, 8–12. doi.org/10.37489/0235-2990-2020-65-9-10-8-12
  22. Классификация Европейской экономической комиссии ЕЭК ООН, https://unece.org/DAM/trans/danger/publi/ghs/ghs_rev07/Russian/03r_Part3.pdf
  23. Pevear D.C., Tull T.M., Seipel M.E., Groarke J.M. Antimicrob. Agents Chemother. 1999, 43, 2109–2115. doi: 10.1128/AAC.43.9.2109.
  24. Smee D.F., Hurst B.L., Evans W.J., Clyde N., Wright S., Peterson Ch., Jung K.-H., Day C.W.J. Virol. Methods. 2017, 246, 51–57. doi: 10.1016/j.jviromet.2017.03.012.
  25. Schmidtke M., Wutzler P., Zieger R., Riabova O.B., Makarov V.A. Antiviral Res. 2009, 81, 56–63. doi: 10.1016/j.antiviral.2008.09.002.
  26. Беккер Х., Беккерт Р., Бергер В., Гевальд К., Генц Ф., Глух Р., Домшке Г., Зайлер Э., Майер Р., Мец П., Мюллер К., Пафель Д., Фангхэнель Э., Фауст Ю., Фишер М., Хабихер В., Шветлик К., Шмидт Д., Шольберг К., Цеппенфельд Г. Органикум. М.: Мир, 2008, 2, 488.
  27. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H.J. Appl. Cryst. 2009, 42, 339–341.
  28. Palatinus L., Chapuis G.J. Appl. Cryst. 2007, 40, 786–790. doi: 10.1107/S0021889807029238
  29. Sheldrick G.M., Acta Cryst. 2008, A64, 112.

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