CHIRAL N-(OCTAHYDRO-2H-CHROMEN-4-YL)-2-(DIALKYLAMINO)ACETAMIDES: SYNTHESIS AND ANALGESIC ACTIVITY

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Based on monoterpenoid (–)-isopulegol a number of new derivatives of octahydro-2H-chromene have been synthesized. The structure of the products obtained was determined by 1H and 13C NMR spectroscopy, high resolution mass spectrometry and X-ray diffraction analysis. It was shown that several synthesized compounds exhibit high analgesic activity in in vivo tests. The highest efficiency in both tests (acetic writhing and hot plate) was shown by (4S)-diastereomers of morpholinoacetamide derivatives of octahydro-2H-chromene.

作者简介

N. Li-Zhulanov

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

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

K. Nikolaichuk

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences; Novosibirsk State University

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk; Russian Federation, 630090, Novosibirsk

Yu. Gatilov

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

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

K. Volcho

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

编辑信件的主要联系方式.
Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

M. Khvostov

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

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

T. Tolstikova

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

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

N. Salakhutdinov

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

Email: volcho@nioch.nsc.ru
Russian Federation, 630090, Novosibirsk

参考

  1. Melnikova I. // Nat. Rev. Drug Discov. 2010. V. 9. P. 589–590. https://doi.org/10.1038/nrd3226
  2. Nizamov I.S., Al’metkina L.A., Gabdullina G.T., Sha-milo, R.R., Sofronov A.V., Nikitina L.E., Lisovskaya S.A., Glushko N.I., Cherkasov R.A. // Russ. Chem. Bull. 2012. V. 61. № 12. P. 2370–2371. https://doi.org/10.1007/s11172-012-0336-7
  3. Zielińska-Błajet M., Feder-Kubis J. // Int. J. Mol. Sci. 2020. V. 21. № 19. P. 7078. https://doi.org/10.3390/ijms21197078
  4. Salakhutdinov N.F., Volcho K.P., Yarovaya O.I. // Pure Appl. Chem. 2017. V. 89. № 8. P. 1105–1117. https://doi.org/10.1515/pac-2017-0109
  5. Do Amaral J.F., Silva M.I.G., Neto M.R.A., Neto P.F.T., Moura B.A., de Melo C.T.V., de Araujo F.L.O., de Sousa D.P., de Vasconcelos P.F., de Vasconcelos S.M.M., de Sou-sa F.C.F. // Biol. Pharm. Bull. 2007. V. 30. P. 1217–1220. https://doi.org/10.1248/bpb.30.1217
  6. Kaimoto T., Hatakeyama Y., Takahashi K., Imagawa T., Tominaga M., Ohta T. // Eur. J. Pain. 2016. V. 20. P. 1155–1165. https://doi.org/10.1002/ejp.840
  7. Lima D.F., Brandão M.S., Moura J.B., Leitão J.M.R.S., Carvalho F.A.A., Miúra L.M.C.V., Leite J.R.S.A., Sou-sa D.P., Almeida F.R.C. // J. Pharmacy Pharmacol. 2012. V. 64. P. 283–292. https://doi.org/10.1111/j.2042-7158.2011.01401.x
  8. Him A., Ozbek H., Turel I., Oner A.C. // Pharmacologyonline. 2008. V. 3. P. 363–369.
  9. Asanova Zh.K., Suleimenov E.M., Atazhanova G.A., Dembitskii A.D., Pak R.N., Dar A., Adekenov S.M. // Pharm. Chem. J. 2003. V. 37. P. 28–30. https://doi.org/10.1023/A:1023699012354
  10. Li Z., Zhang H., Wang Y., Li Y., Li Q., Zhang L. // Front. Mol. Neurosci. 2022. V. 15. 1006908.
  11. Andrade Próspero D.F., Reis Filho A.C., Piauilino C.A., Lopes E.M., de Sousa D.P., de Castro Almeida F.R. // Chem.-Biol. Interact. 2018. V. 293. P. 55–60. https://doi.org/10.1016/j.cbi.2018.07.019
  12. Peana A.T., De Montis M.G., Nieddu E., Spano M.T., D’Aquila P.S., Pippia P. // Eur. J. Pharmacol. 2004. V. 485. P. 165–174. https://doi.org/10.1016/j.ejphar.2003.11.066
  13. Brito R.G., Santos P.L., Prado D.S., Santana M.T., Araújo A.A.S., Bonjardim L.R., Santos M.R.V., de Lucca Júnior W., Oliveira A.P., Quintans-Júnior L.J. // Basic Clin. Pharmacol. Toxicol. 2013. V. 112. P. 215–221. https://doi.org/10.1111/bcpt.12018
  14. Santos P.L., Brito R.G., Oliveira M.A., Quintans J.S.S., Guimarães A.G., Santos M.R.V., Menezes P.P., Serafini M.R., Menezes I.R.A., Coutinho H.D.M., Araújo A.A.S., Quintans-Júnior L.J. // Phytomedicine. 2016. V. 23. P. 948–957. https://doi.org/10.1016/j.phymed.2016.06.007
  15. La Rocca V., da Fonsêca D.V., Silva-Alves K.S., Ferreira-da-Silva F.W., de Sousa D.P., Santos P.L., Quintans-Júnior L.J., Leal-Cardoso J.H., de Almeida R.N. // Basic Clin. Pharmacol. Toxicol. 2017. V. 120. P. 22–29. https://doi.org/10.1111/bcpt.12630
  16. Nishijima C.M., Ganev E.G., Mazzardo-Martins L., Martins D.F., Rocha L.R.M., Santos A.R.S., Hiruma-Lima C.A. // Eur. J. Pharmacol. 2014. V. 736. P. 16–25. https://doi.org/10.1016/j.ejphar.2014.04.029
  17. Nazimova E., Pavlova A., Mikhalchenko O., Il’ina I., Korchagina D., Tolstikova T., Salakhutdinov N. // Med. Chem. Res. 2016. V. 25. № 7. P. 1369–1383. https://doi.org/10.1007/s00044-016-1573-3
  18. Il’ina I.V., Korchagina D.V., Morozova E.A., Tolstikova T.G., Volcho K.P., Salakhutdinov N.F. // Russ. Chem. Bull. 2019. V. 68. № 5. P. 1061–1066. https://doi.org/10.1007/s11172-019-2520-5
  19. Il’ina I.V., Morozova E.A., Korchogina D.V., Volcho K.P., Tolstikova T.G., Salakhutdinov N.F. // Lett. Drug Des. Discov. 2020. V. 17. P. 68–78. https://doi.org/10.2174/1570180816666181114131220
  20. Li-Zhulanov N.S., Pavlova A.V., Korchagina D.V., Gatilov Yu.V., Volcho K.P., Tolstikova T.G., Salakhutdi-nov N.F. // Chem. Heterocycl. Compd. 2020. V. 56. № 7. P. 936–941. https://doi.org/10.1007/s10593-020-02753-x
  21. Sarmah B., Baishya G., Baruah R.K. // RSC Advances. 2014. V. 4. № 43. P. 22387–22397. https://doi.org/10.1039/c4ra02124j
  22. Sidorenko A.Yu., Li-Zhulanov N.S., Mäki-Arvela P., Sandberg T., Kravtsova A.V., Peixoto A.F., Freire C., Volcho K.P., Salakhutdinov N.F., Agabekov V.E., Mur-zin D.Yu. // ChemCatChem. 2020. V. 12. P. 2605–2609. https://doi.org/10.1002/cctc.202000070
  23. Khvostov M.V., Borisov S.A., Tolstikova T.G., Dushkin A.V., Tsyrenova B.D., Chistyachenko Yu.S., Polyakov N.E., Dultseva G.G., Onischuk A.A., An’kov S.V. // Eur. J. Drug Metab. Pharmacokinet. 2017. V. 42. P. 431–440.
  24. Eddy N.B., Leimbach D.J. // J. Pharmacol. Exp. Therap. 1953. V. 107. P. 385–393.

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版权所有 © Н.С. Ли-Жуланов, К.М. Николайчук, Ю.В. Гатилов, К.П. Волчо, М.В. Хвостов, Т.Г. Толстикова, Н.Ф. Салахутдинов, 2023

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