Novel 1,2,4-Triazole- and Tetrazole-Containing 4<i>H</i>-Thiopyrano[2,3-<i>b</i>]quinolines: Synthesis Based on the Thio-Michael/aza-Morita–Baylis–Hillman Tandem Reaction and Investigation of Antiviral Activity
Andrey V. Khramchikhin,
Mariya A. Skryl’nikova,
Maxim A. Gureev,
Vladimir V. Zarubaev,
Iana L. Esaulkova,
Polina A. Ilyina,
Oussama Abdelhamid Mammeri,
Dar’ya V. Spiridonova,
Yuri B. Porozov,
Vladimir A. Ostrovskii
Affiliations
Andrey V. Khramchikhin
Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia
Mariya A. Skryl’nikova
Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia
Maxim A. Gureev
Center of Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, 8, Trubetskaya Street, Bld. 2, 119991 Moscow, Russia
Vladimir V. Zarubaev
Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia
Iana L. Esaulkova
Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia
Polina A. Ilyina
Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 St. Petersburg, Russia
Oussama Abdelhamid Mammeri
Chemical Analysis and Materials Research Center, St. Petersburg State University, 26, Universitetskii Prospect, Petergof, 198504 St. Petersburg, Russia
Dar’ya V. Spiridonova
Research Park, St. Petersburg State University, 26, Universitetskaya Emb. 7/9, 199034 St. Petersburg, Russia
Yuri B. Porozov
Center of Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, 8, Trubetskaya Street, Bld. 2, 119991 Moscow, Russia
Vladimir A. Ostrovskii
Department of Chemistry and Technology of Organic Nitrogen Compounds, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Avenue, 190013 St. Petersburg, Russia
A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4H-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.
