Methods of Synthesis and Antiviral Activity of New 4-Alkyl-3-Nitro-1,4-Dihydroazolo[5,1-c][1,2,4]Triazin-4-ols

Abstract

An azo coupling reaction of α-nitro ketones with 5-diazoazoles was used to obtain 4-alkyl-3-nitro-1,4-dihydroazolo[5,1- с ][1,2,4]triazines, which were characterized with respect to their antiviral activity against influenza and Coxsackie B3 viruses. Supplementary Information The online version contains supplementary material available at 10.1007/s10593-021-02926-2.

Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties

“…It is known that they exhibit inhibitory activity against mixed types of carboxylesterase, 16 that are tuberculostatic 17 and have antiviral activity against influenza and Coxsackie B3 viruses. 15 However, the synthetic strategy has low effectiveness and is laborious. Thus, recovery of the hidden aspects of the reaction of diazoazoles and diazonium salts with enamines would allow their scope to be expanded.…”

“…5 However several examples of dihydroazolo [5,1-c] [1,2,4]triazines were obtained when trisubstituted enamines were used. 5,6,8 1,4-Dihydroazolo [5,1-c] [1,2,4]triazines previously described in the literature [11][12][13][14][15][16][17][18][19] were synthesized through the reaction of diazoazoles with CH-acids and subsequent intramolecular cyclization of hydrazone intermediates. [11][12][13][14][15] These compounds are attractive due to the wide spectrum of their biological activity.…”

“…5,6,8 1,4-Dihydroazolo [5,1-c] [1,2,4]triazines previously described in the literature [11][12][13][14][15][16][17][18][19] were synthesized through the reaction of diazoazoles with CH-acids and subsequent intramolecular cyclization of hydrazone intermediates. [11][12][13][14][15] These compounds are attractive due to the wide spectrum of their biological activity. It is known that they exhibit inhibitory activity against mixed types of carboxylesterase, 16 that are tuberculostatic 17 and have antiviral activity against influenza and Coxsackie B3 viruses.…”