A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4-thiopyrano[2,3-]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.
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November 2022
Chem Heterocycl Compd (N Y)
May 2022
Unlabelled: 3-{[(1-Methyl-1-tetrazol-5-yl)imino]methyl}quinoline-2-thiol and 3-{[(2-methyl-2-tetrazol-5-yl)imino]methyl}quinoline-2-thiol were synthesized. The sequence of the thiol-Michael reaction and the (aza)-Morita-Baylis-Hillman reaction yielded 4-[(1-methyl-1-tetrazol-5-yl)amino]-2-phenyl-4-thiopyrano[2,3-]quinoline-3-carbaldehyde, 4-[(2-methyl-2-tetrazol-5-yl)amino]-2-phenyl-4-thiopyrano[2,3-]-quinoline-3-carbaldehyde, and 4-hydroxy-2-phenyl-4-thiopyrano[2,3-]quinoline-3-carbaldehyde. Cytotoxicity and antiviral activity against the A/Puerto Rico/8/34 (H1N1) influenza virus strain in MDCK cell culture were determined for the obtained compounds.
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