Synthesis, reactions, and antiviral activity of 1-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethanone and pyrido[2′,3′: 3,4]pyrazolo[5,1-c][1,2,4]triazine derivatives

1-(3-Amino-6-methyl-4-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-5-yl)ethanone ( 3) was obtained in very pure state and used as a good starting material for the present study. It diazotized to give the corresponding diazonium salt 9 and also reacted with phenyl isothiocyanate to give the corresponding thiourea derivative 4. Compound 4 was used for the preparation of thiazole derivatives 5-8 via the reaction with active halogen-containing compounds. On the other hand, compound 9 coupled with several active -CH2- containing compounds to afford the corresponding triazine derivatives 10-17. Considering the data from IR, H-1 NMR, mass spectra, and elemental analyses, the chemical structures of the newly synthesized heterocyclic compounds were elucidated. Cytotoxicity, anti-HSV1, and anti-HAV-MBB activity were evaluated for the newly synthesized heterocyclic compounds.