Synthesis of 2-alkyl-1,2,4-triazolo[3,4-a]isoquinolin-2-ium bromides and hexafluorophosphates

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

Alkylation of 1,2,4-triazolo[3,4-a]isoquinolines with 1-bromoalkanes was carried out under microwave synthesis conditions; the resulting 2-alkyl-1,2,4-triazolo[3,4-a]isoquinolin-2-ium bromides were converted into hexafluorophosphates and characterized by high-resolution mass spectrometry, 1H, 13C NMR spectroscopy and X-ray diffraction analysis.

Texto integral

Acesso é fechado

Sobre autores

L. Ermakova

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences

Email: glusha55@gmail.com
ORCID ID: 0009-0008-1397-6631
Rússia, 614068, Perm

N. Leont’ev

Perm State National Research University

Email: glusha55@gmail.com
ORCID ID: 0009-0000-9777-0658
Rússia, 614099, Perm

M. Denisov

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences

Email: glusha55@gmail.com
ORCID ID: 0000-0002-8817-0543
Rússia, 614068, Perm

I. Borisova

Perm State National Research University

Email: glusha55@gmail.com
ORCID ID: 0000-0002-2261-8122
Rússia, 614099, Perm

М. Dmitriev

Perm State National Research University

Email: glusha55@gmail.com
ORCID ID: 0000-0002-0731-3400
Rússia, 614099, Perm

V. Glushkov

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences; Perm State National Research University

Autor responsável pela correspondência
Email: glusha55@gmail.com
ORCID ID: 0000-0001-6493-7351
Rússia, 614068, Perm; 614099, Perm

Bibliografia

  1. Pan Y., Tian R., Chen Y., Wang L., Qin H., Wang J. // Tetrahedron. 2023. Vol. 148. P. 133688. doi 10.1016/ j.tet.2023.133688
  2. Zhang W., Jiang R., Mu Y., Hong Y., Man Y., Yang Z., Tang D. // Tetrahedron Lett. 2023. Vol. 114. P. 154256. doi: 10.1016/j.tetlet.2022.154256
  3. Глушков В.А., Шкляев Ю.В., Майорова О.А., Постаногова Г.А., Фешина Е.В. // ХГС. 2000. Т. 36. С. 380; Glushkov V.A., Shklyaev Yu.V., Maiorova O.A., Postanogova G.A., Feshina E.V. // Chem. Heterocycl. Compd. 2000. Vol. 36. P. 319. doi: 10.1007/BF02256870
  4. Deady L.W., Devine S.M. // J. Heterocycl. Chem. 2004. Vol. 41. P. 549. doi: 10.1002/jhet.5570410411
  5. Chen Z., Chen S., Qui Z., Lin B., Yao Y., Weng Z. // J. Org. Chem. 2024. Vol. 89. P. 7163. doi 10/1021/acs.joc.4c00557
  6. Yount J., Morris M., Henson N., Zeller M., Byrd E.F.C., Piercey D.G. // Chem. Eur. J. 2024. Vol. 30. P. e202400661. doi: 10.1002/chem.202400661
  7. Badr S.M.I., Barwa R.M. // Bioorg. Med. Chem. 2011. Vol. 19. P. 4506. doi: 10.1016/j.bmc.2011.06.024
  8. Zhao P.-L., Duan A.-N., Zou M., Yang H.-K., You W.-W., Wu S.-G. // Bioorg. Med. Chem. Lett. 2012. Vol. 22. P. 4471. doi: 10.1016/j.bmcl.2012.03.023
  9. Yan X., Zhang C., Gao L.-X., Liu M.-M., Yang Y.-T., Yu L.-J., Zhou Y.-B., Milaneh S., Zhu Y.-L., Li J., Wang W.-L. // Eur. J. Med. Chem. 2024. Vol. 265. P. 116027. doi: 10.1016/j.ejmech.2023.116027
  10. Feitosa L.M., Franca R.R.F., Ferreira M. de L.G., Aguiar A.C.C., de Souza G.E., Maluf S.E.C., de Souza J.O., Zapata L., Duarte D., Morais I., Nogueira F., Nonato M.C., Pinheiro L.C.S., Guido R.V.C., Boechat N. // Eur. J. Med. Chem. 2024. Vol. 267. P. 116163. doi 10.1016/ j.ejmech.2024.116163; Ali I., Cha H.J., Lim B., Chae C.H., Youm J., Park W.J., Lee S.H., Kim J.H., Jeong D., Lim J.K., Hwang Y.-H., Roe J.-S., Woo J.-S., Lee K., Choi G. // Eur. J. Med. Chem. 2024. Vol. 265. 116052. doi 10.1016/ j.ejmech.2023.116052
  11. Ali I., Cha H.J., Lim B., Chae C.H., Youm J., Park W.J., Lee S.H., Kim J.H., Jeong D., Lim J.K., Hwang Y.-H., Roe J.-S., Woo J.-S., Lee K., Choi G. // Eur. J. Med. Chem. 2024. Vol. 265. 116052. doi 10.1016/ j.ejmech.2023.116052
  12. Носова Э.В., Копотилова А.Е., Иванькина М.А., Мошкина Т.Н., Копчук Д.С. // Изв. АН. Сер. хим. 2022. Т. 71. № 7. С. 1483; Nosova E.V., Kopotilova A.E., Ivan’kina M.A., Moshkina T.N., Kopchuk D.S. // Russ. Chem. Bull. 2022. Vol. 71. N 7. P. 1483. doi: 10.1007/s11172-022-3554-7
  13. Shtaitz Ya.K., Ladin E.D., Kopchuk D.S., Khalymbadzha I.A., Gaviko V.S., Zyryanov G.V., Antonenko D.V., Ostrovskii V.A., Rusinov V.L. // Russ. J. Gen. Chem. 2024. Vol. 94. P. 749. doi: 10.1134/S1070363224040029
  14. Русинов В.Л., Чарушин В.Н., Чупахин О.Н. // Изв. АН. Сер. хим. 2018. № 4. С. 573; Rusinov V.L., Charushin V.N., Chupakhin O.N. // Russ. Chem. Bull. 2018. Vol. 67. N 4. P. 573. doi: 10.1007/s11172-018-2113-8
  15. Машковский М.Д. Лекарственные средства. М.: Новая волна, 2019. С. 30, 83, 84.
  16. Ермакова Л.С., Грачева В.С., Майорова О.А., Дмитриев М.В., Белоглазова Ю.А., Глушков В.А. // Изв. АН. Сер. хим. 2024. Т. 73. С. 1072; Ermakova L.S., Gracheva V.S., Maiorova O.A., Dmitriev M.V., Beloglazova Yu.A., Glushkov V.A. // Russ. Chem. Bull. 2024. Vol. 73. P. 1072. doi: 10.1007/s11172-024-4222-x
  17. CrysAlisPro, Rigaku Oxford Diffraction, 2022. Version 1.171.42.74a.
  18. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370
  19. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol 71. P. 3. doi: 10.1107/S2053229614024218
  20. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H.J. // Appl. Cryst. 2009. Vol 42. P. 339. doi: 10.1107/S0021889808042726

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Scheme 1.

Baixar (147KB)
Metadados
3. Fig. 1. General view of the bromide molecule 2b according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

Baixar (83KB)
Metadados
4. Fig. 2. General view of the bromide molecule 4a according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

Baixar (98KB)
Metadados

Declaração de direitos autorais © Russian Academy of Sciences, 2024