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

Molecules. 2023. Vol. 28. No. 21. Article 7427.

Khramchikhin A. V., Skryl’nikova M. A., Maxim A. Gureev, Zarubaev V. V., Esaulkova I. L., Ilyina P. A., Mammeri O. A., Spiridonova D. V., Yuri B. Porozov, Ostrovskii V. A.

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.

Keywords: Molecular Docking, antiviral activity, противовирусная активность, молекулярный докинг, 1,2,4-triazole, influenza virus A/Puerto Rico/8/34, tetrazole, thiopyrano[2,3-b]quinolines, тетразол, 1,2,4-триазол, вирус гриппа

Publication based on the results of: Molecular evolution, protein motions and computational molecular modeling (2023)