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Reaction of 6-Oxocyclohexane-1,3-dicarboxamides with Binucleophilic Reagents. Antinociceptive Activity of the Synthesized Hydrazones and 2,3,4,5,6,7-Hexahydro-1H-indazoles

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Abstract

Novel hydrazones and hexahydro-1H-indazole-5-carboxamides were obtained via the reaction of 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxamides with tosylhydrazide, 2,4-dinitrophenylhydrazine, and phenylhydrazine, respectively. The structures of the products were proved by IR and 1H and 13C NMR spectroscopy, as well as X-ray diffraction analysis. The synthesized compounds were tested for antinociceptive activity.

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REFERENCES

  1. Rollas, S., Gulerman, N., and Erdeniz, H., Farmaco, 2002, vol. 57, p. 171. https://doi.org/10.1016/S0014-827X(01)01192-2

    Article  CAS  Google Scholar 

  2. Secci, D., Bizzarri, B., Bolasco, A., Carradori, S., D’Ascenzio, M., Rivanera, D., Mari, E., Polletta, L., and Zicari, A., Eur. J. Med. Chem., 2012, vol. 53, p. 246. https://doi.org/10.1016/j.ejmech.2012.04.006

    Article  CAS  Google Scholar 

  3. Amirthaganesan, S., Aridoss, G., Park, K.S., Lim, K.T., and Jeong, Y.T., Bull. Korean Chem. Soc., 2010, vol. 31, p. 1135. https://doi.org/10.5012/bkcs.2010.31.5.1135

    Article  CAS  Google Scholar 

  4. Dandawate, P., Khan, E., Padhye, S., Gaba, H., Sinha, S., Deshpande, J., Swamy, K.V., Khetmalas, M., Ahmad, A., and Sarkar, F.H., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 3104. https://doi.org/10.1016/j.bmcl.2012.03.060

    Article  CAS  Google Scholar 

  5. Ghodse, A.H. and Galea, S., Side Effects Drugs Annual, 2011, vol. 33, p. 205. https://doi.org/10.1016/B978-0-444-53741-6.00008-8

    Article  Google Scholar 

  6. Sorokin, V.V., Kriven’ko, A.P., Vinogradova, N.A., and Plotnikov, O.P., Pharm. Chem. J., 2001, vol. 35, p. 488. https://doi.org/10.1023/A:1014090608261

    Article  CAS  Google Scholar 

  7. Jain, J., Kumar, Y., Sinha, R., Kumar, R., and Stables, J., Med. Chem., 2011, vol. 7, p. 56. https://doi.org/10.2174/157340611794072689

    Article  CAS  Google Scholar 

  8. Guglielmotti, A., Capezzone, de Joannon, A., Cazzolla, N., Marchetti, M., Soldo, L., Cavallo, G., and Pinza, M., Pharmacol. Res., 1995, vol. 32, p. 369. https://doi.org/10.1016/S1043-6618(05)80042-8

    Article  CAS  Google Scholar 

  9. Said, M.M., Ahmed, A.A.E., and El-Alfy, A.T., Arch. Pharm. Res., 2004, vol. 27, p. 1194. https://doi.org/10.1007/BF02975880

    Article  CAS  Google Scholar 

  10. Gein, V.L., Nosova, N.V., Lezhnina, D.D., Gein, O.N., Voronina, N.V., Starovoytova, M.O., and Dmitriev, M.V., Russ. J. Gen. Chem., 2021, vol. 91, p. 57. https://doi.org/10.31857/S0044460X21010066

    Article  CAS  Google Scholar 

  11. Nosova, N.V., Lezhnina, D.D., Rubtsova, D.D., and Gein, V.L., Butlerov Commun., 2020, vol. 63, p. 31.

    Article  Google Scholar 

  12. Usova, E.B., Lysenko, L.I., Krapivin, G.D., Zavodnik, V.E., and Kul’nevich, V.G., Chem. Heterocycl. Compd., 1997, vol. 33, p. 1259. https://doi.org/10.1007/BF02320324

    Article  CAS  Google Scholar 

  13. CrysAlisPro, Agilent, Technologies, Version, 1.171.37.33.

  14. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  15. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  16. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H.J., Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  17. Gein, V.L., Nosova, N.V., Yankin, A.N., Bazhina, A.Y., and Dmitriev, M.V., Tetrahedron Lett., 2019, vol. 60, p. 1592. https://doi.org/10.1016/j.tetlet.2019.05.023

    Article  CAS  Google Scholar 

  18. Eddy, N.B. and Leimbach, D.J., J. Pharmacol. Exp. Ther., 1953, vol. 107, p. 385.

    CAS  Google Scholar 

  19. Mironov, A.N., Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh veshchestv (Guidelines for Conducting Preclinical Studies of Medicinal Substances), Moscow: Grif and K, 2012, part 1.

  20. Belen’kii, M.L., Elementy kolichestvennoi otsenki farmakologicheskogo effekta (Elements of Quantitative Assessment of the Pharmacological Effect), Leningrad: Medgiz, 1963.

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Funding

The work was financially supported by the Rational Mineral Resource Management Perm Scientific and Educational Center, 2022.

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Correspondence to V. L. Gein.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1192–1199 https://doi.org/10.31857/S0514749222110076.

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Gein, V.L., Lezhnina, D.D., Nosova, N.V. et al. Reaction of 6-Oxocyclohexane-1,3-dicarboxamides with Binucleophilic Reagents. Antinociceptive Activity of the Synthesized Hydrazones and 2,3,4,5,6,7-Hexahydro-1H-indazoles. Russ J Org Chem 58, 1610–1616 (2022). https://doi.org/10.1134/S1070428022110070

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