Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

• DOI: 10.1007/s00044-016-1550-x
• Publication Date: 2016-04-14T06:48:32Z
• Authors: Juan M. Sánchez-C...; Gara R. Barbero; Guillermo Guerrer...; Alexandra G. Durán; Mariola Macías; Manuel A. Rodrígu...; José M. G. Molinillo; Francisco A. Macías
• Keywords: 0301 basic medicine; Potent antifungal; Minimum inhibitory concentration; Biological evaluation; Quinones; Structure–activity relationship; Juglone; Agents; minimum inhibitory concentration; Antifungal; Structure-activity relationship; 1,4-naphthoquinone derivatives; Naphthazarins; 3. Good health; Antibacterial; antibacterial; 03 medical and health sciences; Anticancer; Naphthoquinone; napthoquinone; Naphthopurpurin; antifungal; Inhibition

The synthesis of 1,4-naphthoquinone derivatives is of great interest since these compounds exhibit strong activity as antimalarial, antibacterial, antifungal and anticancer agents. A series of 50 naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity against Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida krusei, Candida parapsilosis and Cryptococcus neoformans using the broth microdilution method. The Candida species were the most susceptible microorganisms. Halogen derivatives of 1,4-naphthoquinone presented strong activity, e.g., 2-bromo-5-hydroxy-1,4-naphthoquinone, which exhibited inhibition at an MIC of 16 A mu g/mL in S. aureus, and 2-chloro-5,8-dihydroxy-1,4-naphthoquinone, with an MIC of 2 A mu g/mL in C. krusei. These compounds showed higher activity against fungi, but the antibacterial activities were very low. The study of structure-activity relationships is very important in the search for new antimicrobial drugs due to the limited therapeutic arsenal.