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

N. S. Li-Zhulanov; Ли-Жуланов Н. С.; K. M. Nikolaichuk; Николайчук К. М.; Yu. V. Gatilov; Гатилов Ю. В.; K. P. Volcho; Волчо К. П.; M. V. Khvostov; Хвостов М. В.; T. G. Tolstikova; Толстикова Т. Г.; N. F. Salakhutdinov; Салахутдинов Н. Ф.

doi:10.31857/S2686953522600751

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

Authors: Li-Zhulanov N.S.¹, Nikolaichuk K.M.¹^,2, Gatilov Y.V.¹, Volcho K.P.¹, Khvostov M.V.¹, Tolstikova T.G.¹, Salakhutdinov N.F.¹
Affiliations:
1. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2. Novosibirsk State University
Issue: Vol 512, No 1 (2023)
Pages: 32-38
Section: ХИМИЯ
URL: https://journals.rcsi.science/2686-9535/article/view/247178
DOI: https://doi.org/10.31857/S2686953522600751
EDN: https://elibrary.ru/UYUMVC
ID: 247178

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

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.

Keywords

isopulegol, Prins–Ritter reaction, octahydro-2H-chromene, analgesic activity

References

Melnikova I. // Nat. Rev. Drug Discov. 2010. V. 9. P. 589–590. https://doi.org/10.1038/nrd3226
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
Zielińska-Błajet M., Feder-Kubis J. // Int. J. Mol. Sci. 2020. V. 21. № 19. P. 7078. https://doi.org/10.3390/ijms21197078
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
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
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
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
Him A., Ozbek H., Turel I., Oner A.C. // Pharmacologyonline. 2008. V. 3. P. 363–369.
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
Li Z., Zhang H., Wang Y., Li Y., Li Q., Zhang L. // Front. Mol. Neurosci. 2022. V. 15. 1006908.
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
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
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
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
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
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
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
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
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
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
Sarmah B., Baishya G., Baruah R.K. // RSC Advances. 2014. V. 4. № 43. P. 22387–22397. https://doi.org/10.1039/c4ra02124j
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
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.
Eddy N.B., Leimbach D.J. // J. Pharmacol. Exp. Therap. 1953. V. 107. P. 385–393.