A series of close analogs of 4-hydroxy-6,7-dimethoxy-2-oxo-N-(pyridin-3-ylmethyl)-1,2-dihydroquinoline-3-carboxamide modified in the benzene moiety of the quinolone nucleus were synthesized to identify the structural fragments determining their analgesic effect. Results of pharmacological tests found that these chemical changes had a relatively weak influence on the analgesic activity of the tested compounds, leading to the conclusion that the modified fragment interacted insignificantly with the biological targets.
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I. V. Ukrainets, A. A. Davidenko, E. V. Mospanova, et al., Chem. Heterocycl. Compd., 46(5), 559 – 568 (2010).
I. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, and S. V. Shishkina, Chem. Heterocycl. Compd., 46(11), 1371 – 1379 (2010).
I. V. Ukrainets, E. V. Mospanova, L. V. Savchenkova, and S. I. Yankovich, Chem. Heterocycl. Compd., 47(1), 67 – 73 (2011).
I. V. Ukrainets, E. V. Mospanova, N. A. Jaradat, et al., Chem. Heterocycl. Compd., 48(9), 1347 – 1356 (2012).
I. V. Ukrainets, K. V. Andreeva, O. V. Gorokhova, and V. N. Kravchenko, Chem. Heterocycl. Compd., 48(12), 1809 – 1816 (2012).
I. V. Ukrainets, O. V. Gorokhova, N. A. Jaradat, et al., in: Pain and Treatment, G. B. Racz and C. E. Noe (eds.), InTech, Rijeka (2014), pp. 21 – 73.
I. V. Ukrainets, E. V. Mospanova, and A. A. Davidenko, Khim.-farm. Zh., 50, No. 6, 15 – 18 (2016); Pharm. Chem. J., 50(6), 365 – 368 (2016).
P. B. Terent?ev and A. P. Stankyavichyus, Mass-spectrometric Analysis of Biologically Active Nitrogenous Bases [in Russian], Mokslas, Vilnius (1987).
I. V. Ukrainets, L. A. Petrushova, S. P. Dzyubenko and G. Sim, Chem. Heterocycl. Compd., 50(1), 103 – 110 (2014).
I. V. Ukrainets, L. V. Sidorenko, L. A. Petrushova, and O. V. Gorokhova, Chem. Heterocycl. Compd., 42(1), 64 – 69 (2006).
H. G. Vogel (ed.), Drug Discovery and Evaluation: Pharmacological Assays, Springer, Berlin (2008), pp. 1030 – 1032.
Ya. A. Sigidin, G. Ya. Shvarts, A. P. Arzamastsev, and S. S. Liberman, Drug Therapy of Inflammation (Experimental and Clinical Pharmacology of Anti-inflammatory Drugs) [in Russian], Meditsina, Moscow (1988), pp. 62 – 63.
V. E. Kuz?min, A. G. Artemenko, E. N. Muratov, et al., in: Recent Advances in QSAR Studies, T. Puzyn, M. Cronin, and J. Leszczynski (eds.), Springer, New York (2009), pp. 127 – 172.
I. Sushko, S. Novotarskyi, R. Korner, et al., J. Chem. Inf. Model., 50(12), 2094 – 2111 (2010).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 52, No. 10, pp. 8 – 12, October, 2018.
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Ukrainets, I.V., Mospanova, E.V., Bereznyakova, N.L. et al. Modification of the Benzene Moiety in the Quinolone Nucleus of 4-Hydroxy-6,7-Dimethoxy-2-Oxo-N-(Pyridin-3-Ylmethyl)-1,2-Dihydroquinoline-3-Carboxamide as an Attempt to Enhance its Analgesic Activity. Pharm Chem J 52, 825–829 (2019). https://doi.org/10.1007/s11094-019-1908-8
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DOI: https://doi.org/10.1007/s11094-019-1908-8