Abstract
2-{[5-Aryl-2-oxofuran-3(2H)-ylidene]amino}thiophene-3-carboxylic acid derivatives reacted with substituted amines to give new N-substituted 4-aryl-4-oxo-2-[(3-thiophen-2-yl)amino]but-2-enamides. Antinociceptive activity of the synthesized compounds was studied.
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REFERENCES
Bozorov, K., Nie, L.F., Zhao, J., and Aisa, H.A., Eur. J. Med. Chem., 2017, vol. 140, p. 465. https://doi.org/10.1016/j.ejmech.2017.09.039
Rossetti, A., Bono, N., Candiani, G., Meneghetti, F., Roda, G., and Sacchetti, A., Chem. Biodivers., 2019, vol. 16, p. e1900097. https://doi.org/10.1002/cbdv.201900097
Regal, M.K.A., Shaban, S.S., and El-Metwally, S.A., J. Heterocycl. Chem., 2019, vol. 56, p. 226. https://doi.org/10.1002/jhet.3399
Puthran, D., Poojary, B., Purushotham, N., Harikrishna, N., Nayak, S.G., and Kamat, V., Heliyon, 2019, vol. 5, p. e02233. https://doi.org/10.1016/j.heliyon.2019.e02233
Baravkar, S.B., Wagh, M.A., Nawale, L.U., Choudhari, A.S., Bhansali, S., Sarkar, D., and Sanjayan, G.J., Chem. Select, 2019, vol. 4, p. 2851. https://doi.org/10.1002/slct.201803370
Vasileva, A.Y., Vaganov, V.Y., Shipilovskikh, S.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2018, vol. 54, p. 582. https://doi.org/10.1134/s1070428018040115
Thomas, J., Jecic, A., Vanstreels, E., Berckelaer, L., Romagnoli, R., Dehaen, W., Liekens, S., and Balzarini, J., Eur. J. Med. Chem., 2017, vol. 132, p. 219. https://doi.org/10.1016/j.ejmech.2017.03.044
Thomas, J., Jana, S., Sonawane, M., Fiey, B., Balzarini, J., Liekens, S., and Dehaen, W., Org. Biomol. Chem., 2017, vol. 15, p. 3892. https://doi.org/10.1039/c7ob00707h
Pavase, L.S. and Mane, D.V., Med. Chem. Res., 2016, vol. 25, p. 2380. https://doi.org/10.1007/s00044-016-1692-x
Wang, X., Chen, D., Yu, S., Zhang, Z., Wang, Y., Qi, X., Fu, W., Xie, Z., and Ye, F., Chem. Biol. Drug. Des., 2016, vol. 87, p. 499. https://doi.org/10.1111/cbdd.12687
Javadi, F. and Tayebee, R., Microporous Mesoporous Mat., 2016, vol. 231, p. 100. https://doi.org/10.1016/j.micromeso.2016.05.025
Akbarzadeh, A. and Dekamin, M.G., Green Chem. Lett. Rev., 2017, vol. 10, p. 315. https://doi.org/10.1080/17518253.2017.1380234
Puterova, Z., Krutosikova, A., and Vegh, D., Arkivoc, 2010, vol. 1, p. 209. https://doi.org/10.3998/ark.5550190.0011.105
Tyuneva, A. V., Igidov, N.M., Koryagina, N.N., Borodin, A.Y., Zakhmatov, A.V., Makarov, A.S., Toksarova, Y.C., and Rubtsov, A.E., Russ. J. Org. Chem., 2011, vol. 47, p. 258. https://doi.org/10.1134/S1070428011020163
Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2003, vol. 39, p. 869. https://doi.org/10.1023/B:RUJO.0000003167.28537.71
Shipilovskikh, S.A., Rubtsov, A.E., and Zalesov, V.V., Chem. Heterocycl. Compd., 2009, vol. 45, p. 658. https://doi.org/10.1007/s10593-009-0334-3
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2015, vol. 50, p. 1853. https://doi.org/10.1134/s1070428014120288
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. Chem. Bull., 2015, vol. 63, p. 2205. https://doi.org/10.1007/s11172-014-0722-4
Shipilovskikh, S.A., Shipilovskikh, D.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2017, vol. 53, p. 137. https://doi.org/10.1134/s1070428017010274
Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 298. https://doi.org/10.1134/s1070428014020286
Siutkina, A.I., Igidov, N.M., Dmitriev, M.V., Makhmudov, R.R., and Novikova, V.V., Russ. J. Gen. Chem., 2019, vol. 89, p. 1388. https://doi.org/10.1134/s1070363219070065
Gein, V.L., Zamaraeva, T.M., Gorgopina, E.V., Igidov, N.M., Bobrovskaya, O.V., and Dmitriev, M.V., Russ. J. Gen. Chem., 2018, vol. 88, p. 832. https://doi.org/10.1134/s1070363218040321
Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2007, vol. 43, p. 735. https://doi.org/10.1134/S1070428007050156
Bykov, R.A., Trapeznikova, N.N., Balandina, S.Y., Komarova, O.A., Makhmudov, R.R., Pulina, N.A., Sobin, F.V., and Rubtsov, A.E., Pharm. Chem. J., 2018, vol. 52, p. 415. https://doi.org/10.1007/s11094-018-1833-2
Pulina, N.A., Sobin, F.V., Kozhukhar’, V.Y., Makhmudov, R.R., Rubtsov, A.E., and Naugol’nykh, E.A., Pharm. Chem. J., vol. 48, p. 11. https://doi.org/10.1007/s11094-014-1034-6
Shipilovskikh, S.A., Makhmudov, R.R., Lupach, D.Y., Pavlov, P.T., Babushkina, E.V., and Rubtsov, A.E., Pharm. Chem. J., 2013, vol. 47, p. 366. https://doi.org/10.1007/s11094-013-0960-z
Eddy, N.B. and Leimbach, D.J., J. Pharmacol. Exp. Ther., 1953, vol. 107, no. 3, p. 385.
Mironov, A.N., Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh veshchestv (Guidelines for preclinical studies of drugs), Moscow: Grif i K, 2012, pt. 1, p. 509.
Belen’kii, M.L., Elementy kolichestvennoi otsenki farmakologicheskogo effekta (Elements for Quantifying the Pharmacological Effect), Leningrad: Medgiz, 1963.
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This work was financially supported by the Russian Foundation for Basic Research (project no. 19-43-590023).
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Shipilovskikh, S.A., Vaganov, V.Y., Makhmudov, R.R. et al. Synthesis and Antinociceptive Activity of N-Substituted 4-Aryl-4-oxo-2-[(3-thiophen-2-yl)amino]but-2-enamides. Russ J Gen Chem 90, 583–589 (2020). https://doi.org/10.1134/S1070363220040040
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DOI: https://doi.org/10.1134/S1070363220040040