Nucleophilic substitution of nitro group in nitrotriazolotriazines as a model of potential interaction with cysteine-containing proteins

@article{Rusinov2015NucleophilicSO,
  title={Nucleophilic substitution of nitro group in nitrotriazolotriazines as a model of potential interaction with cysteine-containing proteins},
  author={Vladimir L. Rusinov and Irina M Sapozhnikova and E. N. Ulomskii and N. R. Medvedeva and Vladimir V. Egorov and Oleg I. Kiselev and E. G. Deeva and Andrey V. Vasin and Oleg N. Chupakhin},
  journal={Chemistry of Heterocyclic Compounds},
  year={2015},
  volume={51},
  pages={275-280}
}
The nucleophilic susbstitution of nitro group in [1,2,4]triazolo[5,1-c][1,2,4]triazinones upon treatment with cysteine and glutathione was studied as a model for the interaction with thiol groups of virus proteins, which mimics the metabolic transformations of antiviral drug Triazavirin® and its derivatives. 

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References

SHOWING 1-10 OF 10 REFERENCES
Nitroazines. 9. Characteristic features of nucleophilic substitution of the nitro group in dihydroazolo[5,1-c] [1,2,4]triazines
The reaction of 6-nitro-7-oxo-4,7-dihydroazolo[5,1-c]-1,2,4-triazines with O-, N-, and S-nucleophiles leads to the corresponding 6-substituted compounds. In the reaction ofExpand
Synthesis and antiviral activity of nucleoside analogs based on 1,2,4-triazolo[3,2-c][1,2,4]triazin-7-ones
Nucleoside analogs containing hydroxybutyl, hydroxyethoxymethyl, allyloxymethyl, and propargyloxymethyl fragments were synthesized based on 1,2,4-triazolo[3,2-c][1,2,4]triazin-7-ones isosteric toExpand
Azolo[5,1-c]-1,2,4-triazines as a new class of antiviral compounds
Synthetic methods, reactivity, and the properties of a new class of antiviral compounds, pyrazolo-, imidazo-, 1,2,4-triazolo[5,1-c]-1,2,4-triazinones, tetrazolo[5,1-b]-1,2,4-triazinones, andExpand
Nitroazines. 7. Alkylation of 6-nitro-7-oxo-4,7-dihydroazolo[5,1-c][1,2,4]-triazines and identification of the products
Reaction of 6-nitro-7-oxo-4,7-dihydroazolo[5,1-c][1,2,4]triazines with methyl iodide or dimethyl sulfate affords the N-methyl derivatives, no O-alkylation products being found. The effect of theExpand
Protective groups in organic synthesis
  • P. Hodge
  • Chemistry, Materials Science
  • 1981
Provides comprehensive information on the most useful protective groups for the hydroxyl, amino, carboxyl, carbonyl, and sulfhydryl groups. Discusses the chemistry of the classes of protectiveExpand
Antiviral Properties, Metabolism, and Pharmacokinetics of a Novel Azolo-1,2,4-Triazine-Derived Inhibitor of Influenza A and B Virus Replication
TLDR
TZV suppressed the replication of influenza virus in cell culture and in chicken chorioallantoic membranes, and it protected mice from death caused by type A and B influenza viruses, and TZV was also effective against a rimantadine-resistant influenza virus strain and against avian influenza A virus H5N1 strains. Expand
Antiviral agents active against influenza A viruses
  • E. Clercq
  • Medicine
  • Nature Reviews Drug Discovery
  • 2006
TLDR
This article reviews agents that have been shown to have activity against influenza A viruses and discusses their therapeutic potential, and also describes emerging strategies for targeting these viruses. Expand
Influenza Pandemic 2009/2010: Antiviral Therapy and Treatment Tactics [in Russian]
  • Research Institute of Influenza: St-Petersburg,
  • 2010
Basics in Biochemistry [in Russian
  • Moscow: Agar,
  • 1999