Synthesis and properties of (+)-ketopinic and (-)-camphanic acids esters bearing a nitrogen-containing heterocycle

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 three-stage method was proposed for the synthesis of (1 S )-(+)-camphor-10-sulfonic acid, (+)-ketopinic and (-)-camphanic acids esters containing a saturated nitrogen-containing heterocycle. It was found that (1 S )-(+)camphor-10-sulfonic acid esters undergo destruction with elimination of the sulfonic acid group in substitution reactions involving nitrogen-containing heterocycles. Esters of (+)-ketopinic and (-)-camphanic acids were formed during the proposed synthetic route, but undergo transesterification under column chromatography conditions. Quantum chemical calculations showed that the destruction of the ester bond in the case of (+)-ketopinic and (-)-camphanic acids requires less energy than the breaking of a similar bond in (-)-borneol esters. It was revealed that the internal bond strength index (IBSI) for the alkyl C-O bond in (-)-borneol esters is higher than in (+)-ketopinic and (-)-camphanic acid esters. Antiviral properties against the H1N1 influenza virus were studied for derivatives of (+)-ketopinic and (-)-camphanic acids.

Sobre autores

A. Sokolova

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: asokolova@nioch.nsc.ru

O. Yarovaya

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

L. Kuzminykh

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

M. Ilyina

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

S. Borisevich

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Ya. Esaulkova

Pasteur St. Petersburg Research Institute of Epidemiology and Microbiology

V. Zarubaev

Pasteur St. Petersburg Research Institute of Epidemiology and Microbiology

N. Salakhutdinov

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

Bibliografia

  1. Talele T.T. // J. Med. Chem. 2018. Vol. 61. Р. 2166. doi: 10.1021/acs.jmedchem.7b00315
  2. Sokolova A.S., Yarovaya O.I., Semenova M.D., Shtro A.A., Orshanskaya I.R., Zarubaev V.V., Salakhutdinov N.F. // MedChemComm. 2017. Vol. 8. Р. 960. doi: 10.1021/acs.joc.8b00655
  3. Sokolova A.S., Yarovaya O.I., Zybkina A.V., Mordvinova E.D., Shcherbakova N.S., Zaykovskaya A.V., Baev D.S., Tolstikova T.G., Shcherbakov D.N., Pyankov O.V., Maksyutov R.A., Salakhutdinov N.F. // Eur. J. Med. Chem. 2020. Vol. 207. P. 112726. doi: 10.1016/j.ejmech.2020.112726
  4. Sokolova A.S., Yarovaya O.I., Shtro A.A., Klabukov A.M., Galochkina A.V, Nikolaeva V., Petukhova G.D., Borisevich S.S., Khamitov E.M., Salakhutdinov N.F. // Pharmaceuticals. 2022. Vol. 15. N 11. P. 1390. doi: 10.3390/ph15111390
  5. Yarovaya O.I., Shcherbakov D.N., Borisevich S.S., Sokolova A.S., Gureev M.A., Khamitov E.M., Rudometova N.B., Zybkina A.V., Mordvinova E.D., Zaykovskaya A.V., Rogachev A.D., Pyankov O.V., Maksyutov R.A., Salakhutdinov N.F. // Viruses. 2022. Vol. 14. N 6. P. 1295. doi: 10.3390/v14061295
  6. Sokolova A.S., Putilova V.P., Yarovaya O.I., Zybkina A.V., Mordvinova E.D., Zaykovskaya A.V., Shcherbakov D.N., Orshanskaya I.R., Sinegubova E.O., Esaulkova I.L., Borisevich S.S., Bormotov N.I., Shishkina L.N., Zarubaev V.V., Pyankov O.V., Maksyutov R.A., Salakhutdinov N.F. // Molecules. 2021. Vol. 26. N 8. P. 2235. doi: 10.3390/molecules26082235. 2019
  7. Соколова А.С., Баранова Д.В., Яровая О.И., Зыбкина А.В., Мордвинова Е.Д., Зайковская А.В., Баев Д.С., Толстикова Т.Г., Щербаков Д.Н., Пьянков О.В., Максютов Р.А., Салахутдинов Н.Ф. // Изв. АН. Сер. xим. 2023. Т. 72. № 10. С. 2536
  8. Sokolova A.S., Baranova D.V., Yarovaya O.I., Zybkina A.V., Mordvinova E.D., Zaykovskaya A.V., Baev D.S., Tolstikova T.G., Shcherbakov D.N., Pyankov O.V., Maksyutov R.A., Salakhutdinov N.F. // Russ. Chem. Bull. 2023. Vol. 72. P. 2536. doi: 10.1007/s11172-023-4056-y
  9. Соколова А.С., Баранова Д.В., Яровая О.И., Баев Д.С., Полежаева О.А., Зыбкина А.В., Щербаков Д.Н., Толстикова Т.Г., Салахутдинов Н.Ф. // Изв. АН. Сер. хим. 2019. Т. 68, N 5. C. 1041
  10. Sokolova A.S., Baranova D.V., Yarovaya O.I., Baev D.S., Polezhaeva O.A., Zybkina A.V., Shcherbakov D.N., Tolstikova T.G., Salakhutdinov N.F. // Russ. Chem. Bull. 2019. Vol. 68. N 5. P. 1041. doi: 10.1007/s11172-019-2517-0
  11. Huynh U., McDonald S. L., Lim D., Uddin Md.N., Wengryniuk S.E., Dey S., Coltart D.M. // J. Org. Chem. 2018. Vol. 83. N 21. Р. 12951. doi: 10.1021/acs.joc.8b00655
  12. Gerlach H., Kappes D., Boeckman R.K., Jr., Maw G. // Org. Synth. Coll. 1998. Vol. 9. Р.151. doi: 10.15227/orgsyn.071.0048
  13. Gomez-Bombarelli R., Calle E., Casado J. // J. Org. Chem. 2013. Vol. 78. Р. 6880. doi: 10.1021/jo4002596
  14. Silva P.L., Silva C.M., Guimarães L., Pliego J.R., Jr. // Theor. Chem. Acc. 2015. Vol. 134. P. 1591. doi: 10.1007/s00214-014-1591-5
  15. Klein J., Khartabil H., Boisson J.C., Contreras-Garciá J., Piquemal J.P., Hénon E. // J. Phys. Chem. (A). 2020. Vol. 124. N 9. P. 1850. doi: 10.1021/acs.jpca.9b09845
  16. Lu T., Chen F. // J. Comput. Chem. 2012. Vol. 33. N 5. P. 580. doi: 10.1002/jcc.22885
  17. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A.V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H.P., Ortiz J.V., Fox D.J. Gaussian 16 Rev. C.01. Wallingford, CT. 2016.
  18. Becke A.D. // J. Chem. Phys. 1993. Vol. 98. N 7. P. 5648. doi: 10.1063/1.464913
  19. Lee C., Yang W., Parr R.G. // Phys. Rev. (B). 1988. Vol. 37. N 2. P. 785. doi: 10.1103/PhysRevB.37.785
  20. Krishnan R., Binkley J.S., Seeger R., Pople J.A. // J. Chem. Phys. 1980. Vol. 72. P. 650. doi: 10.1063/1.438955
  21. Baronio C.M., Barth A. // J. Phys. Chem. (B). 2020. Vol. 124. N 9. P. 1703. doi: 10.1021/acs.jpcb.9b11793
  22. Cheng H., Yan D., Wu L., Liang P., Cai Y., Li L. // Acta Crystallogr. (C). 2022. Vol. 78. N 10. P. 531. doi: 10.1107/S2053229622008592

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar

Declaração de direitos autorais © Russian Academy of Sciences, 2023