Abstract
According to the in silico consensus activity prediction, a series of 3,6-disubstituted 1,2,4,5-tetrazines were synthesized as promising inhibitors of the Maillard reaction. In addition to the studies of antiglycation activity, a comparative in vitro evaluation of the effect of the synthesized compounds on the ADP-induced rabbit platelet aggregation model was carried out. Compounds with antiglycation and antiplatelet activities significantly higher than that of the reference drugs, aminoguanidine and acetylsalicylic acid, were revealed.
Similar content being viewed by others
References
Pat. RU 2462466, Byul. Izobret. [Invention Bull.], 2012, No. 27 (in Russian).
R. I. Ishmetova, N. K. Ignatenko, I. A. Belyaninova, S. G. Tolschina, A. V. Korotina, P. A. Slepukhin, N. P. Evstigneeva, N. V. Zil’berberg, P. G. Amineva, N. V. Kungurov, G. L. Rusinov, O. N. Chupakhin, Russ. Chem. Bull., 2015, 64, 2100.
Pat. RU 2527258, Byul. Izobret. [Invention Bull.], 2014, No. 24 (in Russian).
F. Xu, Zh.-Zh. Yang, Zh.-Lu Ke, Li-M. Xi, Qi-D. Yan, W.-Q. Yang, L.-Q. Zhu, F.-L. Lin, W.-Ke Lv, H.-G. Wu, J. Wang, H.-Bo Li, Bioorg. Med. Chem. Lett., 2016, 26, 4580.
F. M. A. Altalbawy, E. S. S. Darwish, Asian J. Chem., 2011, 23, 2951–2955.
R. I. Ishmetova, N. K. Ignatenko, A. V. Korotina, I. N. Ganebnykh, P. N. Slepukhin, V. A. Babkova, N. A. Gerasimova, N. P. Evstigneeva, N. V. Zil’berberg, N. V. Kungurov, G. L. Rusinov, A. A. Spasov, O. N. Chupakhin, Russ. Chem. Bull., 2018, 67, 2079.
Pat. RU 2668971, Byul. Izobret. [Invention Bull.], 2018, No. 28 (in Russian).
G. L. Rusinov, N. I. Latosh, R. I. Ishmetova, M. A. Kravchenko, I. N. Ganebnykh, V. A. Sokolov, O. N. Chupakhin, Pharm. Chem. J., 2005, 39, 8.
Pat. RU 2479311, Byul. Izobret. [Invention Bull.], 2013, No. 11 (in Russian).
Pat. RU 2642882, Byul. Izobret. [Invention Bull.], 2018, No. 4 (in Russian).
D. Nhu, S. Dufly, V. M. Avery, A. Hughes, J. B. Baell, Bioorg. Med. Chem. Lett., 2010, 20, 4496.
J. Li, J. Chen, C. L. Ricupero, R. P. Hart, M. S. Schwartz, A. Kusnecov, K. Herrup, Nat. Med., 2012, 18, 783.
R. I. Ishmetova, N. K. Ignatenko, I. N. Ganebnykh, S. G. Tolshchina, A. V. Korotina, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, Russ. Chem. Bull., 2014, 63, 1423.
S. G. Tolshchina, A. G. Vyakhireva, N. K. Ignatenko, R. I. Ishmetova, I. N. Ganebnykh, P. A. Slepukhin, G. L. Rusinov, Russ. Chem. Bull., 2009, 58, 1281.
R. I. Ishmetova, N. I. Latosh, I. N. Ganebnykh, N. K. Ignatenko, S. G. Tolshchina, G. L. Rusinov, Russ. J. Org. Chem., 2009, 45, 1102.
M. D. Coburn, G. A. Buntain, B. W. Harris, M. A. Hiskey, K. Y. Lee, D. G. Ott, J. Heterocycl. Chem., 1991, 28, 2049.
G. L. Rusinov, N. I. Latosh, I. N. Ganebnykh, R. I. Ishmetova, N. K. Ignatenko, O. N. Chupakhin, Russ. J. Org. Chem., 2006, 42, 757.
D. A. Filimonov, V. V. Poroykov, Zhurn. ross. khim. ob-va im. D. I. Mendeleeva [Mendeleev Chem. J.], 2006, 50, 66 (in Russian).
P. M. Vassiliev, A. A. Spasov, A. N. Kochetkov, V. V. Vorfolomeeva, L. R. Yanaliev, in Mishen’-oriyentirovannyi poisk antidiabeticheskikh sredstv [Target-oriented Search for Antidiabetic Drugs], Eds A. A. Spasov, V. I. Petrov, Volgograd State Medical University, Volgograd, 2016, pp. 126–181 (in Russian).
P. M. Vassiliev, A. A. Spasov, V. A. Kosolapov, A. F. Kucheryavenko, N. A. Gurova, V. A. Anisimova, in Application of Computational Techniques in Pharmacy and Medicine. Challenges and Advances in Computational Chemistry and Physics, Eds L. Gorb, V. Kuz’min, E. Muratov, Springer, Dordrecht—Heidelberg—New York—London, 2014, Vol. 17, p. 369.
P. M. Vassiliev, A. A. Spasov, V. A. Kuznetsova, A. N. Kochetkov, V. V. Frantseva, L. R. Yanalieva, Tez. dokl. XXII Rossiyskogo Natsional’nogo kongressa “Chelovek i lekarstvo” [Proc. of XXII Russian National Congress “Human and Medicine”] (April 7–10, 2015, Moscow, Russia), Moscow, 2015, p. 184 (in Russian).
Yu. A. Sokolov, Prognozirovaniye biologicheskoi aktivnosti soyedinenii s ispolzovaniyem kvantovo-khimicheskikh metodov [Prediction of the Biological Activity for Compounds Using Quantum Chemical Methods], Belarus. nauka, Minsk, 2008, 309 pp. (in Russian).
P. M. Vassiliev, 2nd Russian Conference on Medicinal Chemistry (MedChem-2015) (July 5–10, 2015, Novosibirsk, Russia), Novosibirsk, 2015, p. 302.
Rukovodstvo po doklinicheskomu issledovaniyu lekarstvennykh sredstv [Guidelines for Preclinical Drug Research], Ed. A. N. Mironova, part 1, Grif and K, Moscow, 2012, 944 pp. (in Russian).
N. I. Latosh, G. L. Rusinov, I. N. Ganebnykh, O. N. Chupakhin, Russ. J. Org. Chem., 1999, 35, 1363.
Author information
Authors and Affiliations
Corresponding author
Additional information
This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (State task No. AAAA-A19-119011790134-1) and performed using the equipment of the Shared Access Center for Spectroscopy and Analysis of Organic Compounds of the Ural Branch of RAS.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0768–0773, April, 2020.
Rights and permissions
About this article
Cite this article
Ishmetova, R.I., Babkov, D.A., Kucheryavenko, A.F. et al. In silico consensus activity prediction, rational synthesis, and evaluation of antiglycation and antiplatelet activities of 3,6-disubstituted 1,2,4,5-tetrazines. Russ Chem Bull 69, 768–773 (2020). https://doi.org/10.1007/s11172-020-2831-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-2831-6