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

Annotation. 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. Quantum-chemical 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 proper-ties. The antimicrobial activity of the synthesized compounds against the strains Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 was studied. © 2025 Elsevier B.V., All rights reserved.