Novel 1,2,4-Triazole- and Tetrazole-Containing 4 H -Thiopyrano[2,3- b ]quinolines: Synthesis Based on the Thio-Michael/aza-Morita-Baylis-Hillman Tandem Reaction and Investigation of Antiviral Activity.

Autor: Khramchikhin AV; Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia., Skryl'nikova MA; Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia.; Saint Petersburg Federal Research Center of the Russian Academy of Sciences (SPC RAS), 39, 14th Line, 199178 St. Petersburg, Russia., Gureev MA; Center of Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, 8, Trubetskaya Street, Bld. 2, 119991 Moscow, Russia.; St. Petersburg School of Physics, Mathematics and Computer Science, HSE University, 16, Soyuza Pechatnikov Str., 190008 St. Petersburg , Russia., Zarubaev VV; Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia., Esaulkova IL; Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia., Ilyina PA; Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia., Mammeri OA; Chemical Analysis and Materials Research Center, St. Petersburg State University, 26, Universitetskii Prospect, Petergof, 198504 St. Petersburg, Russia., Spiridonova DV; Research Park, St. Petersburg State University, 26, Universitetskaya Emb. 7/9, 199034 St. Petersburg, Russia., Porozov YB; Center of Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, 8, Trubetskaya Street, Bld. 2, 119991 Moscow, Russia.; St. Petersburg School of Physics, Mathematics and Computer Science, HSE University, 16, Soyuza Pechatnikov Str., 190008 St. Petersburg , Russia., Ostrovskii VA; Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia.; Saint Petersburg Federal Research Center of the Russian Academy of Sciences (SPC RAS), 39, 14th Line, 199178 St. Petersburg, Russia.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2023 Nov 04; Vol. 28 (21). Date of Electronic Publication: 2023 Nov 04.
DOI: 10.3390/molecules28217427
Abstrakt: A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4 H -thiopyrano[2,3- b ]quinolines using a new combination of the thio-Michael and aza-Morita-Baylis-Hillman reactions was developed. Target compounds were evaluated for their cytotoxicities and antiviral activities against influenza A/Puerto Rico/8/34 virus in MDCK cells. The compounds showed low toxicity and some exhibited moderate antiviral activity. Molecular docking identified the M2 channel and polymerase basic protein 2 as potential targets. We observed that the antiviral activity of thiopyrano[2,3- b ]quinolines is notably affected by both the nature and position of the substituent within the tetrazole ring, as well as the substituent within the benzene moiety of quinoline. These findings contribute to the further search for new antiviral agents against influenza A viruses among derivatives of thiopyrano[2,3- b ]quinoline.
Databáze: MEDLINE
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