Synthesis and study of antimicrobial activity of amides and salts of 4-aminoantipyrine – derivatives of 1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acids

By the condensation of 1-oxo-1,2,3,6,7,7a-hexahydrohydro3a,6-epoxyisoindole-7-carboxylic acids with 4-aminoantipyrine or N-methyl-1-[5-(p-tolyl)isodiesol-3-yl]methylamine in the presence of dicyclohexylbisodiimidine in a dichloromethane medium, corresponding amides with a yield of 67–78 % were synthesized. By the interaction of 1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoisoindole-7-carboxylic acids with 4-aminoantipyrine or N-methyl-1-[5-(p-tolyl)isodioxol-3-yl]methylamine in methanol, corresponding ammonic salts with a yield of 93–97 % were obtained. Quantumchemical modelling of energy parameters and electronic structure of synthesized compounds by ab initio method, with the level of theory B3LYP1/MIDI, was carried out in order to preliminary assess their potential antibacterial and antiviral properties. The antimicrobial activity of the synthesized compounds against the strains Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 was studied.

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