Abstract
The reaction of unsubstituted acetoacetamide with aromatic aldehydes in ethanol in the presence of piperidine gave 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxamides and 4-aryl-5-acetyl-2-hydroxy-2-methyl-6-oxopiperidine-3-carboxamides. Structures of the obtained compounds were proved using IR, 1H and 13C NMR spectroscopy methods. The synthesized compounds were tested for antimicrobial and analgesic activities.
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REFERENCES
Gein, V.L., Nosova, N.V., Yankin, A.N., Bazhina, A.Y., and Dmitriev, M.V., Tetrahedron Lett., 2019, vol. 60, no. 24, p. 1592. https://doi.org/10.1016/j.tetlet.2019.05.023
Gein, V.L., Voronina, E.V., Gein, N.V., and Krivenko, A.P., Pharm. Chem. J., 2002, vol. 36, no. 3, p. 131. https://doi.org/10.1023/A:1019678210738
Gein, V.L., Zorina, A.A., Gein, N.V., Voronina, E.V., and Krivenko, A.P., Pharm. Chem. J., 2005, vol. 39, no. 4, p. 188. https://doi.org/10.1007/s11094-005-0114-z
Gein, V.L., Vagapov, A.V., Nosova, N.V., Voronina, E.V., Vakhrin, M.I., and Krivenko, A.P., Pharm. Chem. J., 2010, vol. 44, no. 5, p. 245. https://doi.org/10.1007/s11094-010-0440-7
Gein, V.L., Odegova, T.F., Yankin, A.N., and Nosova, N.V., Pharm. Chem. J., 2015, vol. 49, no. 4, p. 246. https://doi.org/10.1007/s11094-015-1264-2
Sorokin, V.V., Krivenko, A.P., Vinogadova, N.A., and Plotnikov, O.P., Pharm. Chem. J., 2001, vol. 35, no. 9, p. 488. https://doi.org/10.1023/A:1014090608261
Gein, V.L., Levandovskaya, E.V., Nosova, N.V., Antonova, N.V., Voronina, E.V., Vakhrin, M.I., and Krivenko, A.P., Pharm. Chem. J., 2007, vol. 41, no. 12, p. 643. https://doi.org/10.1007/s11094-008-0043-8
Krivenko, A.P. and Sorokin, V.B., Russ. J. Org. Chem., 1999, vol. 35, no. 8, p. 1097.
Gein, V.L., Levandovskaya, E.B., Nosova, N.V., Vakhrin, M.I., Kriven’ko, A.P., and Aliev, Z.G., Russ. J. Org. Chem., 2007, vol. 43, no. 7, p. 1096. https://doi.org/10.1134/S1070428007070275
Sengupta, T., Gayen, K.S., Pandit, P., and Maiti, D.K., Chem. Eur. J., 2012, vol. 18, p. 1905. https://doi.org/10.1002/chem.201103354
Sidorov, K.K., Toksikologiya novykh promyshlennykh khimicheskikh veshchestv (Toxicology of New Industrial Chemicals), 1973, № 13, p. 47.
Prozorovskii, V.V., Prozorovskaya, M.P., and Demchenko, V.M., Farmakol. Toksikol., 1978, vol. 41, no. 4, p. 497.
Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (Guidelines for Conducting Preclinical Studies of Drugs), Mironov, A.N., Bunyatyan, N.D., Vasiliev, A.N., Verstakova, O.L., Zhuravleva, M.V., Lepakhin, V.K., Korobov, N.V., Merkulov, V.A., Orekhov, S.N., Sakaeva, I.V., Uteshev, D.B., and Yavorskii, A.N., Eds., Moscow: Grif i K, 2012, pt 1.
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Nosova, N.V., Lezhnina, D.D., Gein, O.N. et al. Synthesis and Biological Activity of 2-Aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxamides. Russ J Gen Chem 90, 1817–1822 (2020). https://doi.org/10.1134/S1070363220100011
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DOI: https://doi.org/10.1134/S1070363220100011