Synthesis, structure, and analgesic activity of methyl (3R*,4S*)-4-aryl-2-oxo-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates

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

A series of new methyl (3R*,4S*)-4-aryl-2-oxo-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates was obtained by three-component condensation of dimethyl malonate, aromatic aldehyde, and 1H-benzimidazole-2-amine in methanol in the presence of piperidine. The structure of the obtained compounds was determined by 1H, 13C NMR spectroscopy and X-ray diffraction analysis. The analgesic activity of the synthesized compounds was studied.

Texto integral

Acesso é fechado

Sobre autores

K. Podchezertseva

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID ID: 0009-0009-7473-5505
Rússia, 614990, Perm

N. Buzmakova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID ID: 0000-0003-3171-0438
Rússia, 614990, Perm

T. Zamaraeva

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Autor responsável pela correspondência
Email: tanyapgfa@yandex.ru
ORCID ID: 0000-0002-9932-9628
Rússia, 614990, Perm

N. Slepova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID ID: 0000-0003-3924-3715
Rússia, 614990, Perm

М. Dmitriev

Perm State National Research University

Email: tanyapgfa@yandex.ru
ORCID ID: 0000-0002-8817-0543
Rússia, 614068, Perm

Bibliografia

  1. Федотов В.В., Русинов В.Л., Уломский Е.Н., Мухин Е.М., Горбунов Е.Б., Чупахин О.Н. // ХГС. 2021. Т. 57. № 4. С. 383; Fedotov V.V., Rusinov V.L., Ulomsky E.N., Mukhin E.M., Gorbunov E.B., Chupakhin O.N. // Chem. Heterocycl. Compd. 2021. Vol. 57. N 4. P. 383. doi: 10.1007/6034
  2. Sondhi S.M., Rajvanshi S., Johar M., Bharti N., Azam A., Singh A.K. // Eur. J. Med. Chem. 2002. Vol. 37. N 10. P. 835. doi: 10.1016/s0223-5234(02)01403-4.
  3. Mardazad N., Khorshidi A., Shojaei A.F. // RSC Adv. 2021. Vol. 11. P. 12349. doi: 10.1039/d1ra01005k
  4. Tran P.H., Thi Bui T.-P., Bach Lam X.-Q., Thi Nguyen X.-T. // RSC Adv. 2018. Vol. 8. P. 36392. doi: 10.1039/c8ra07256f
  5. Kaur N., Kaur K., Raj T., Kaur G., Singh A., Aree T., Park S.-J., Kim T.-J., Singh N., Jang D.O. // Tetrahedron. 2015. Vol. 71. P. 332. doi: 10.1016/j.tet.2014.11.039
  6. Шихалиев Х.С., Крыльский Д.В., Потапов А.Ю., Крысин М.Ю., Трефилова И.Н. // Изв. вузов. Сер. хим. и хим. технол. 2004. Т. 47. Вып. 3. С. 149.
  7. Abedini M., Shirini F., Mousapour M., Goli Jolodar O. // Res. Chem. Intermed. 2016. Vol. 42. P. 6221. doi: 10.1007/s11164-016-2456-4
  8. Risley V.A., Henry S., Kosyrikhina M.V., Manzanares M.R., Payan I., Downer C.D., Hellmann C.C., Van Slambrouck S., Frolova L.V. // Chem. Heterocycl. Compd. 2014. Vol. 50. N 2. P. 185. doi: 10.1007/1469
  9. Chavan P., Salve A., Shelke R., Pansare D. // Lett. Appl. NanoBioSci. 2022. Vol. 11. N 1. P. 2996. doi: 10.33263/LIANBS111.29963005
  10. Подчезерцева К.В., Замараева Т.М., Слепова Н.В., Дмитриев М.В. // ЖОХ. 2024. Т. 94. № 6. С. 699. doi: 10.31857/S0044460X24060034
  11. CrysAlisPro, Rigaku Oxford Diffraction, 2022, Version 1.171.42.74a.
  12. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370
  13. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. P. 3. doi: 10.1107/S2053229614024218
  14. 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
  15. Руководство по проведению доклинических исследований лекарственных средств / Под ред. А.Н. Миронова, Н.Д. Бунятян, А.Н. Васильева, О.Л. Верстаковой, М.В. Журанлевой, В.К. Лепахина, Н.В. Коробова, В.А. Меркулова, С.Н. Орехова, И.В. Сакаевой, Д.Б. Утешева, А.Н. Яворского. М.: Гриф и К, 2012. Ч. 1. 944 с.
  16. Беленький М.Л. Элементы количественной оценки фармакологического эффекта. Л.: Медгиз, 1963. С. 81.

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Scheme 1. Ar = 4-BrC6H4 (1), 4-(CH3)2NC6H4 (2), 4-(C2H5)2NC6H4 (3), 3-NO2C6H4 (4), 4-CH3OC6H4 (5), 2,4-(CH3O)2C6H3 (6).

Baixar (67KB)
Metadados
3. Fig. 1. General view of the dimer molecule of compound 2 according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

Baixar (141KB)
Metadados

Declaração de direitos autorais © Russian Academy of Sciences, 2024