Antiviral Activity of (1S,9aR)-1-[(1,2,3-Triazol-1-yl)methyl]octahydro-1H-quinolizines from the Alkaloid Lupinine
Nurmaganbetov Z.S. Nurkenov O.A. Khlebnikov A.I. Fazylov S.D. Seidakhmetova R.B. Tukhmetova Z.K. Takibayeva A.T. Khabdolda G. Rakhimberlinova Z.B. Kaldybayeva A.K. Shults E.E.
December 2024Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2024#29Issue 23
Influenza is a disease of significant morbidity and mortality. The number of anti-influenza drugs is small; many of them stimulate the appearance of resistant strains. This article presents the results of assessing the antiviral activity of 1,2,3-triazole-containing derivatives of alkaloid lupinine for their ability to suppress the reproduction of orthomyxoviruses (influenza viruses: A/Vladivostok/2/09 (H1N1) and A/Almaty/8/98 (H3N2)). The ability of (1S,9aR)-1-[(1,2,3-triazol-1-yl)-methyl]octahydro-1H-quinolizines with aryl-, 4-((4-formylphenoxy)methyl)- or 4-((3-tert-butyl-5-ethyl-2-hydroxy-benzoyloxy)methyl)- substituents at the C-4 position of the triazole ring to reduce the infectivity of the virus when processing virus-containing material was established, indicating good prospects for the studied compounds as virucidal agents affecting extracellular virions. The experimental results demonstrated that the triazolyl lupinine derivatives exhibited varying degrees of affinity for both hemagglutinin and neuraminidase proteins. Furthermore, these compounds demonstrated inhibitory effects on the replication of influenza viruses with different antigenic subtypes. The obtained biological data are in agreement with the results of molecular docking, which showed strong binding energies of the investigated compounds under study with biological targets—hemagglutinin and neuraminidase proteins. Following the evaluation of antiviral efficacy among the studied triazolyl derivatives of lupinine, four compounds have been identified for subsequent comprehensive in vitro and in vivo investigations to further elucidate their antiviral properties.
(1S,9aR)-1-[(1,2,3-triazol-1-yl)methyl]octahydro-1H-quinolizines , alkaloid lupinine , antiviral activity , molecular docking , orthomyxoviruses , rimantadine , Tamiflu
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Laboratory of Synthesis of Biologically Active Substances, Institute of Organic Synthesis and Coal Chemistry, Karaganda, 100008, Kazakhstan
School of Pharmacy, Karaganda Medical University, Karaganda, 100008, Kazakhstan
Kizhner Research Center, Tomsk Polytechnic University, Tomsk, 634050, Russian Federation
Department of Clinical Pharmacology and Evidence-Based Medicine, Karaganda Medical University, Karaganda, 100008, Kazakhstan
Department of Biomedicine, Karaganda Medical University, Karaganda, 100008, Kazakhstan
Department of Chemistry and Chemical Technology, A. Saginov Karaganda Technical University, Karaganda, 100027, Kazakhstan
Department of Pharmaceutical and Toxicological Chemistry, S.D. Asfendiyarov Kazakh National Medical University, Almaty, 050012, Kazakhstan
Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090, Russian Federation
Laboratory of Synthesis of Biologically Active Substances
School of Pharmacy
Kizhner Research Center
Department of Clinical Pharmacology and Evidence-Based Medicine
Department of Biomedicine
Department of Chemistry and Chemical Technology
Department of Pharmaceutical and Toxicological Chemistry
Novosibirsk Institute of Organic Chemistry
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