Naphthoquinones are important compounds with several biological properties including the antibacterial action. 2-(2,4-dichloroanilino)-1,4-naphthoquinone (3a), 2-(2,4-difluoroanilino)-1,4-naphthoquinone (3b) and 2-(anilino)-1,4-naphthoquinone (3c) compounds were obtained by Michael 1,4-type addition reaction of anilines to 1,4-naphthoquinone ring. Ultrasound Assisted Synthesis (UAS), Microwave Assisted Synthesis (MAS) methods were performed as alternative sources of activation. The results showed that UAS promoted the reaction and provide the best yields. The antibacterial effect against the strains Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Salmonella choleraesius was performed. Hemolysis and antioxidant assays were described to complete the biological discussion. The compound 3a was the most active against E. coli with an inhibition of 99.62%. The derivatives showed a doses-responsive effect in the hemolysis assay, and the compound 3a was the least toxic. The percentage of DPPH radical trapping in the antioxidant activity exhibited results under 15%. Therefore, according these results it is possible to obtained 2-(anilino)-1,4-naphthoquinone derivatives using methodologies more efficient as ultrasound attached to the green chemistry. The synthesis of new naphthoquinone compounds is an alternative to the global problem of bacterial drug resistant to antibiotics.\nKeywords: 2-(anilino)-1,4-naphthoquinone, antibacterial activity, E. coli.

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