Aldol-crotonic condensation reactions of 3,5-diacetyl-2,6-dimethylpyridine with various aldehydes were used to synthesize bisazachalcone derivatives, which were subsequently cyclized with hydrazine hydrate in acetic acid, leading to the respective bisderivatives of 4,5-dihydro-1H-pyrazole. The reactions of 3,5-diacetyl-2,6-dimethylpyridine with some hydrazides also provided the respective bishydrazones. The analgesic activity of the obtained derivatives was tested.
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Torchy, S.; Cordonnier, G.; Barbry, D.; Vanden Eynde, J. J. Molecules 2002, 7, 528.
Kulakov, I. V.; Karbainova, A. A.; Shulgau, Z. T.; Seilkhanov, T. M.; Gatilov, Y. V.; Fisyuk, A. S. Chem. Heterocycl. Compd. 2017, 53, 1094. [Khim. Geterotsikl. Soedin. 2017, 53, 1094.]
Verma, S.; Srivastava, A. K.; Pandey, O. P. PharmaTutor 2018, 6, 22.
Shringare, S. N.; Chavan, H. V.; Bhale, P. S.; Dongare, S. B.; Mule, Y. B.; Patil, S. B.; Bandgar, B. P. Med. Chem. Res. 2018, 27, 1226.
Adib, M.; Rajai-Daryasarei, S.; Pashazadeh, R.; Jahani, M.; Amanlou, M. Synlett 2018, 1583.
Amr, A. E. G. E.; Maigali, S. S.; Abdulla, M. M. Monatsh. Chem. 2008, 139, 1409.
Kozmík, V.; Lhoták, P.; Odlerová, Ž.; Paleček, J. Collect. Czech. Chem. Commun. 1998, 63, 698.
Pattan, S. R.; Rasal, V. P.; Venkatramana, N. V.; Khade, A. B.; Butle, S. R.; Jadhav, S. G.; Desai, B. G.; Manvi, F. V. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2007, 46, 698.
Pattan, S. R.; Purohit, S. S.; Rasal, V. P.; Mallya, S.; Marihal, S. C.; Khade, A. B.; Paschapur, M. S. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2008, 47, 626.
Arumugam, P.; Perumal, P. T. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2008, 47, 1084.
(a) Sashidhara, K. V.; Kumar, M.; Kumar, A. Tetrahedron Lett. 2012, 53, 2355. (b) Manna, F.; Chimenti, F.; Fioravanti, R.; Bolasco, A.; Secci, P. C.; Ferlini, C.; Scambia G. Bioorg. Med. Chem. Lett. 2005, 15, 4632. (c) Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Cirilli, R.; La Torre, F.; Alcaro, S.; Ortuso, F.; Langer, T. Curr. Med. Chem. 2006, 13, 1411. (d) Jagtap, P. G.; Degterev, A.; Choi, S.; Keys, H.; Yuan, J.; Cuny, G. D. J. Med. Chem. 2007, 50, 1886.
Zhang, J.; Zhang, M.; Cao, W.; Song, L.; Qian, Q.; Tan, J. Heteroat. Chem. 2009, 20, 123.
Patole, J.; Sandbhor, U.; Padhye, S.; Deobagkar, D. N.; Ansonc, C. E.; Powell, A. Bioorg. Med. Chem. Lett. 2003, 13, 51.
Mashkovskii, M. D. Drugs; Novaya Volna: Moscow, 2012, p. 856.
Rollas, S.; Küçükgüzel, S. G. Molecules 2007, 12, 1910.
Manikandan, V.; Balaji, S.; Senbagam, R.; Vijayakumar, R.; Rajarajan, M.; Vanangamudi, G.; Thirunarayanan, G. Int. J. Adv. Chem. 2017, 5, 17.
Popiołek, Ł.; Biernasiuk, A. Saudi Pharm. J. 2017, 25, 1097.
Machado, P.; Rosa, F. A.; Rossatto, M.; Sant'Anna, G. D. S.; Sauzem, P. D.; Silva, R. M. S.; Martins, M. A. P. ARKIVOC 2007, (xvi), 281.
Khiati, Z.; Othman, A. A.; Guessas, B. S. Afr. J. Chem. 2007, 60, 20.
Guide to conducting preclinical studies of medicines [in Russian]; Mironov, A. N., Ed.; Grif i K.: Moscow, 2012, part 1, p. 746.
European Convention for the Protection of Vertebrate Animals Used for Experimental and other Scientific Purposes (ETS 123); Strasbourg, 1986.
This work was performed with financial support from the Committee for Sciences, Ministry of Education and Science, Republic of Kazakhstan (grant No. AP05131602).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(1), 47–51
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Oleshchuk, A.L., Karbainova, A.A., Krivoruchko, T.N. et al. Synthesis and biological activity of 3,5-diacetyl-2,6-dimethylpyridine derivatives. Chem Heterocycl Comp 55, 47–51 (2019). https://doi.org/10.1007/s10593-019-02417-5
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DOI: https://doi.org/10.1007/s10593-019-02417-5