1H-1,2,4-Triazolo-5-diazonium salts in the synthesis of new 6H-benzopyrano[4,3-e][1,2,4]triazolo[5,1-c]-[1,2,4]triazine-6-ones and [1,2,4]triazolo[5',1':3,4][1,2,4]-triazino[6,5-c]quinoline-6(7H)-ones

Cover Page

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

A convenient synthetic approach to the synthesis of new 2-R-6Н-benzopyrano[4,3-е][1,2,4]triazolo[5,1-с][1,2,4]triazin-6-ones and 2-R-[1,2,4]triazolo[5',1':3,4][1,2,4]triazino[6,5-c]quinolin-6(7H)-ones based on 3-R-1H-1,2,4-triazolo-5-diazonium salts with 2H-1-benzopyran-2,4(3H)dione and 2,4(1H,3H)-quinolinedione.

Full Text

Restricted Access

About the authors

M. N. Mawlood

Voronezh State University

Email: pistones@mail.ru
ORCID iD: 0009-0007-7293-1823
Russian Federation, pl. Universitetskaya, 1, Voronezh

A. Yu. Potapov

Voronezh State University

Author for correspondence.
Email: pistones@mail.ru
ORCID iD: 0000-0001-8084-530X
Russian Federation, pl. Universitetskaya, 1, Voronezh

Kh. S. Shikhaliev

Voronezh State University

Email: pistones@mail.ru
ORCID iD: 0000-0002-6576-0305
Russian Federation, pl. Universitetskaya, 1, Voronezh

References

  1. Viegas-Junior C., Danuello A., da Silva Bolzani V., Barreiro E.J., Manssour Fraga C.A. Curr. Med. Chem. 2007, 14, 1829–1852. doi: 10.2174/092986707781058805
  2. Gao F., Ye L., Wang Y., Kong F., Zhao Sh., Xiao J., Huang G. Eur. J. Med. Chem. 2019, 183, 111678. doi: 10.1016/j.ejmech.2019.111678
  3. Meunier B. Acc. Chem. Res. 2008, 41, 69–77. doi: 10.1021/ar7000843
  4. Kartsev V., Shikhaliev Kh.S., Geronikaki A., Medvedeva S.M., Ledenyova I.V., Krysin M.Yu., Petrou A., Ciric A., Glamoclija J., Sokovic M. Eur. J. Med. Chem. 2019, 175, 201–214. doi: 10.1016/j.ejmech.2019.04.046
  5. Gao J., Zhang, Z., Zhang B., Mao Q., Dai X., Zou Q., Lei Y., Feng Y., Wang S. Bioorg. Chem. 2020, 95, 103564. doi: 10.1016/j.bioorg.2019.103564
  6. Novichikhina N., Ilin I., Tashchilova A., Sulimov A., Kutov D., Ledenyova I., Krysin M., Shikhaliev Kh., Gantseva A., Gantseva E., Podoplelova N., Sulimov V. Molecules 2020, 25, 1889. doi: 10.3390/molecules25081889
  7. Djemoui A., Naouri A., Ouahrani M.R., Djemoui D., Lahcene S., Lahrech M.B., Boukenna L., Albuquerque H.M.T., Saher L., Rocha D.H.A., Monteiro F.L., Helguero L.A., Bachari K., Talhi O., Silva A.M.S. J. Mol. Struct. 2020, 1204, 127487. doi: 10.1016/j.molstruc.2019.127487
  8. Новичихина Н.П., Шестаков А.С., Потапов А.Ю., Кошелева Е.А., Шаталов Г.В., Вережников В.Н., Вандышев Д.Ю., Леденева И.В., Шихалиев Х.С. Изв. А.Н. Сер. хим. 2020, № 4, 787–792. [Novichikhina N.P., Shestakov A.S., Potapov A.Yu.,. Kosheleva E.A, Shatalov G.V., Verezhnikov V.N., Vandyshev D.Yu., Ledeneva I.V., Shikhaliev Kh.S. Russ. Chem. Bull. 2020, № 4, 787–792]
  9. Welsch M.E., Snyder S.A., Stockwell B.R. Curr. Opin. Chem. Biol. 2010, 14, 347–361. doi: 10.1016/j.cbpa.2010.02.018
  10. DeSimone R.W., Currie K.S., Mitchell S.A., Darrow J.W., Pippin D.A. Comb. Chem. High Throughput Screen 2004, 7, 473–494. doi: 10.2174/1386207043328544
  11. Sarveswari S., Vijayakumar V., Siva R., Priya R. Appl. Biochem. Biotechnol. 2015, 175 (1), 43–64. doi: 10.1007/s12010-014-1256-9
  12. Sabbah D.A., Hishmah B., Sweidan K., Bardaweel S., AlDamen M., Zhong H.A., Khalaf R.A., Ameerah (Hasan Ibrahim), Al-Qirim T., Sheikha G.A., Mubarak M.S. Anticancer Agents Med. Chem. 2018, 18, 263–276. doi: 10.2174/1871520617666170911171152
  13. Dodia N., Shah A. Indian J. Het. Chem. 1999, 9(2), 139–142.
  14. Tedesco R., Shaw A.N., Bambal R., Chai D., Concha N.O., Darcy M.G., Dhanak D., Fitch D.M., Gates A., Gerhardt W.G., Halegoua D.L., Han C., Hofmann G.A., Johnston V.K., Kaura A.C., Liu N., Keenan R.M., Lin-Goerke J., Sarisky R.T., Wiggall K.J., Zimmerman M.N., Duffy K.J. J. Med. Chem. 2006, 49, 971–983. doi: 10.1021/jm050855s
  15. Furugohri T., Isobe K., Honda Y., Kamisato-Matsumoto C., Sugiyama N., Nagahara T., Morishima Y., Shibano T.J. Thromb. Haemostasis. 2008, 6, 1542–1549. doi: 10.1111/j.1538-7836.2008.03064.x
  16. Fjellström O., Akkaya S., Beisel H.G., Eriksson P.O., Erixon K., Gustafsson D., Jurva U., Kang D., Karis D., Knecht W., Nerme V., Nilsson I., Olsson T., Redzic A., Roth R., Sandmark J., Tigerstrom A., Oster L. PLoS One. 2015, 10, 1–42. doi: 10.1371/journal.pone.0113705
  17. Obaidullah A.J., Al-Horani R.A. Cardiovasc. Hematol. Agents Med. Chem. 2017, 15, 40–48. doi.10.2174/1871525715666170529093938
  18. Amin K.M., Gawad N.M.A., Rahman D.E.A., El Ashry M.K.E. Bioorg. Chem. 2014, 52, 31–43. doi: 10.1016/j.bioorg.2013.11.002
  19. Verespy S., Mehta A.Y., Afosah, D., Al-Horani R.A., Desai U.R. Sci Rep. 2016, 6, 24043. doi: 10.1038/srep24043
  20. Riyadh S.M., Kheder N.A., Asiry A.M. Monatsh. Chem. 2013, 144, 1559–1567. doi: 10.1007/s00706-013-1028-1
  21. Abdelhamid A.O., Gomha S.M., El-Enany W.A.M.A. J. Heterocycl. Chem. 2019, 56, 426–432. doi: 10.1002/jhet.3415
  22. Уломский Е.Н., Деев У.Н., Шестакова Е.С., Руси-нов В.Л., Чупахин О.Н. Изв. АН, Сер. хим. 2002, 51, 1594–1600. [Ulomskii E.N., Deev S.L., Shestakova T.S., Rusinov V.L., Chupakhin O.N. Russ. Chem. Bull. 2002, 51, 1737–1743.] doi: 10.1023/A:1021320025860
  23. Abdelhamid A.O., Zohdy H.F., Zaida M.M. Ind. J. Chem. 2000, 39B, 202.
  24. Crespan E., Alexandrova L., Khandazhinskaya A., Jasko M., Kukhanova M., Villani G., Hübscher U., Spadari S., Maga G. Nucleic Acids Res. 2007, 35, 45–57. doi: 10.1093/nar/gkl1016
  25. Русинов В.Л., Уломский Е.Н., Чупахин О.Н., Забаиров М.М., Кпапустин А.В., Митин А.В., Жураветский М.И., Виноград И.А. Хим.-фарм. ж. 1990, 24, 41–44. [Rusinov V.L., Ulomskii E.N., Chupakhin O.N., Zubairov M.M., Kapustin A.B., Mitin N.I., Zhiravetskii M.I., Vinograd I.A. Pharm. Chem. J. 1990, 24, 646–650.] doi: 10.1007/BF00767030
  26. Русинов В.Л., Уломский Е.Н., Чупахин О.Н., Чарушин В.Н. Изв. АН, Сер. хим. 2008, 57, 967–996. [Rusinov V. L., Ulomskii E.N., Chupakhin O.N., Charushin V.N. Russ. Chem. Bull. 2008, 57, 985–1014.]. doi: 10.1007/s11172–008–0130–8
  27. Jashari A., Imeri F., Ballazhi L., Shabani A., Mikhova B., Drager G., Popovski E., Huwiler A. Bioorg. Med. Chem. 2014, 22, 2655–2661. doi: 10.1016/j.bmc.2014.03.026

Supplementary files

Supplementary Files
Action
1. JATS XML
2. Fig. 1. Hybrid molecules of 2-R-6H-[1]benzopyrano[4,3-e][1,2,4]triazolo[5,1-c][1,2,4]triazin-6-one (a) and 2-R-[1,2,4]triazolo[5',1':3,4][1,2,4]triazino[6,5-c]quinolin-6(7H)-one (b).

Download (250KB)
3. Scheme 1

Download (772KB)
4. Scheme 2

Download (867KB)
5. Content

Download (46KB)

Copyright (c) 2025 Russian Academy of Sciences