Abstract
Structural analogs of a promising antituberculous agent, ethyl 5-methyl-7-(thiophen-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate have been synthesized by three-component condensations of various aromatic or hetaromatic aldehydes with several β-dicarbonyl compounds (CH acids) and 1H-1,2,4-triazol-5-amine or 1H-pyrazol-5-amine. The obtained compounds have been evaluated for tuberculostatic activity, and structure-activity relations have been analyzed.
Similar content being viewed by others
References
Kumar, V., Patel, S., and Jain, R., Med. Res. Rev., 2018, vol. 38, p. 684. doi https://doi.org/10.1002/med.21454
Filatova, L.Yu., Klyachko, N.L., and Kudryashova, E.V., Russ. Chem. Rev., 2018, vol. 87, p. 374. doi https://doi.org/10.1070/RCR4740
Shakya, N., Garg, G., Agrawal, B., and Kumar, R., Pharmaceuticals, 2012, vol. 5, p. 690. doi https://doi.org/10.3390/ph5070690
Wang, H., Lee, M., Peng, Zh., Blázquez, B., Lastochkin, E., Kumarasiri, M., Bouley, R., Chang, M., and Mobashery, Sh., J. Med. Chem., 2015, vol. 58, p. 4194. doi https://doi.org/10.1021/jm501831g
Yu, W., Goddard, C., Clearfield, E., Mills, C., Xiao, T., Guo, H., Morrey, J.D., Motter, N.E., Zhao, K., Block, T.M., Cuconati, A., and Xu, X., J. Med. Chem., 2011, vol. 54, p. 5660. doi https://doi.org/10.1021/jm200696v
Afonkina, E.S., Pereyaslavskaya, E.S., Potemkin, V.A., Grishina, M.A., Rusinov, G.L., and Fedorova, O.V., J. Struct. Chem., 2009, vol. 50, p. 982. doi https://doi.org/10.1007/s10947-009-0146-4
Fedorova, O.V., Titova, Yu.A., Kravchenko, M.A., Skornyakov, S.N., Medvinskii, I.D., Rusinov, G.L., and Charushin, V.N., RU Patent no. 2654463 C1, 2017; Byull. Izobret., 2018, no. 14.
Fedorova, O.V., Zhidovinova, M.S., Rusinov, G.L., and Ovchinnikova, I.G., Russ. Chem. Bull., Int. Ed., 2003, vol. 52, p. 1768. doi https://doi.org/10.1023/B:RUCB.0000012380.78140.26
Zhidovinova, M.S., Cand. Sci. (Chem.) Dissertation, Yekaterinburg, 2005.
Svetlik, J., Veizerová, L., Mayer, T., and Catarinella, M., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 4073. doi https://doi.org/10.1016/j.bmcl.2010.05.085
Chebanov, V.A., Saraev, V.E., Desenko, S.M., Chernenko, V.N., Knyazeva, I.V., Groth, U., Glasnov, T.N., and Kappe, O., J. Org. Chem., 2008, vol. 73, p. 5110. doi https://doi.org/10.1021/jo800825c
Platonova, A.G., Mazhukina, O.A., and Fedotova, O.V., J. Struct. Chem., 2015, vol. 56, p. 1205. doi https://doi.org/10.1134/S0022476615060311
Wisniewska, C., Koszelewski, D., Zysk, M., Kłossowski, S., Zadło, A., Brodzka, A., and Ostaszewski, R., Eur. J. Org. Chem., 2015, vol. 24, p. 5432. doi https://doi.org/10.1002/ejoc.201500676
Acknowledgments
The authors thank the Ural Research Institute of Phthisiopulmonology (Yekaterinburg) for performing biological studies in vitro.
Funding
This study was performed under financial support by the Russian Science Foundation (project no. 15-13-00077-P).
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 85th anniversary
Russian Text© The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 6, pp. 871–878.
Conflict of Interests
The authors declare no conflict of interests.
Rights and permissions
About this article
Cite this article
Titova, Y.A., Filatova, E.S., Fedorova, O.V. et al. 4-(Het)aryl-4,7-dihydroazolopyrimidines and Their Tuberculostatic Activity. Russ J Org Chem 55, 775–781 (2019). https://doi.org/10.1134/S107042801906006X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107042801906006X