The previously described L-argininium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide monohydrate and piperidinium 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide, which has not been described previously, were synthesized as promising antiviral drugs. A detailed comparison of the crystal structures of these two compounds was performed. It is shown that the replacement of the L-arginine cation with piperidinium one leads to a serious reorganization of the system of intermolecular hydrogen bonds in the solid state, which, in our opinion, can have a significant impact on the interaction of the new drug with biological targets. Thus, by comparing the X-ray structural analysis data, the probability of the influence of the nature of the counterion on the biological effect of the drug was demonstrated.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
De Clercq, E.; Field, H. J. Br. J. Pharmacol. 2006, 147, 1.
Kresge, N.; Simoni, R. D.; Hill, R. L. J. Biol. Chem. 2008, 283, e11.
Ustianowski, A.; Arends, J. E. Infect. Dis. Ther. 2015, 4, 145.
Kiselev, О. I. Chemomedications and influenza chemotherapy [in Russian]; Rostok: Sankt-Petersburg, 2011.
Deeva, E. G. Influenza. On the verge of a pandemic [in Russian]; GEOTAR-Media: Moscow, 2008.
Iuliano, D.; Roguski, K. M.; Chang, H. H.; Muscatello, D. J.; Palekar, R.; Tempia, S.; Cohen, C.; Gran, J. M.; Schanzer, D.; Cowling, B. J.; Wu, P.; Kyncl, J.; Ang, L. W.; Park, M.; Redlberger-Fritz, M.; Yu, H.; Espanhain, L.; Krishnan, A.; Emukule, G.; van Asten, L.; Pereira de Silva, S.; Aungkulanon, S.; Buchholz, U.; Widdowson, M.-A.; Breese, J. S. Lancet2017, 391, 1285.
Rath, B.; Penttinen, P. Incidence, Severity and Impact of Influenza: a joint meeting organised by the ISIRV Epidemiology Group and ECDC, Stockholm, 2019; Euro Surveill.2019, 24(23), 1900348.
Artem'ev, G. A.; Bondarev, V. P.; Borisevich, S. V.; Vasin, A. V.; Voinkov, E. K.; Glavatskikh, S. A.; Deeva, E. G.; Egorov, V. V.; Zabelina, O. N.; Zagorodnikova, K. A.; Ivanova, A. V.; Ivantsova, M. N.; Kiselev, O. I.; Kozhikhova, K. V.; Kozitsina, A. N.; Konovalova, N. I.; Kopchuk, D. S.; Kotovskaya, S. K.; Loginova, S. Ya.; Maksimov, V. A.; Malakhova, N. A.; Matern, A. I.; Medvedeva, N. R.; Mel'nikova, T. I.; Mirgorodskaya, O. A.; Mironov, M. A.; Nekrasov, P. A.; Rusinov, V. L.; Sapozhnikova, I. M.; Saraeva, S. Yu.; Svalova, T. S.; Slepukhin, P. A.; Sorokin, P. V.; Tokareva, M. I.; Tumashov, A. A.; Ulomskiy, E. N.; Tsmokalyuk, A. N.; Charushin, V. N.; Chupakhin, O. N.; Shaldzhan, A. A.; Sharkov, G. V.; Shablakova, A. S.; Petrov, A. Yu. Triazavirin, a new generation antiviral drug [in Russian]; Postovsky Institute of Organic Synthesis: Yekaterinburg, 2016.
Chupakhin, О. N.; Charushin, V. N.; Rusinov, V. L.; Ylomskii, E. N.; Kotovskaya, S. K.; Kiselev, О. I.; Deeva, E. G.; Savateev, K. V.; Borisov, S. S. RU Patent 20130116765.
Deeva, E. G.; Shevchik, Yu. I.; Shaldzhan, A. А.; Zagorodnikova, K. А.; Tumashov, А. А.; Baklykov, А. V.; Kotovskaya, S. K.; Chupakhin, О. N.; Charushin, V. N.; Rusinov, V. L.; Kopchuk, D. S. Razrabotka i registratsiya lekarstvennykh sredstv2018, 3, 172.
Savateev, K. V.; Ulomsky, E. N.; Fedotov, V. V.; Rusinov, V. L.; Sivak, K. V.; Lyubishin, M. M.; Kuzmich, N. N.; Aleksandrov, A. G. Russ. J. Bioorg. Chem. 2017, 43, 421. [Bioorg. Khim.2017, 43, 402.]
Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.
Palatinus, L.; Chapuis, G. J. Appl. Crystallogr. 2007, 40, 786.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr.2008, A64, 112.
This work was supported by the Ministry of Education and Science of the Russian Federation (grant 4.6351.2017 / 8.9).
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary information file containing detailed crystallographic information parameters of compounds 1, 2 is available at the journal website at http://link.springer.com/journal/10593.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 989–992
Electronic supplementary material
ESM 1
(PDF 360 kb)
Rights and permissions
About this article
Cite this article
Slepukhin, P.А., Voinkov, E.K., Ulomskiy, E.N. et al. Synthesis and X-ray structural studies of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-а]pyrimidine L-arginine and piperidine salts. Chem Heterocycl Comp 55, 989–992 (2019). https://doi.org/10.1007/s10593-019-02567-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-019-02567-6