1. Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes
- Author
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Lucia Sessa, Stefano Piotto, Rosita Diana, Gabriel Torrens, Simona Concilio, Carlos Juan, Ugo Caruso, Pio Iannelli, Piotto, Stefano, Concilio, Simona, Sessa, Lucia, Diana, Rosita, Torrens, Gabriel, DE MARTIN, JUAN CARLOS, Caruso, Ugo, and Iannelli, Pio
- Subjects
Staphylococcus aureus ,estructura molecular ,synthesis ,listeria monocytogenes ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Biology ,010402 general chemistry ,medicine.disease_cause ,01 natural sciences ,Article ,azo-compound ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Listeria monocytogenes ,Drug Discovery ,medicine ,Organic chemistry ,Phenols ,Physical and Theoretical Chemistry ,Escherichia coli ,Listeria monocytogene ,Aza Compounds ,Molecular Structure ,compuestos aza ,010405 organic chemistry ,Synthesi ,Medicine (all) ,Gram-positive antibacterial ,Organic Chemistry ,biology.organism_classification ,Antimicrobial ,0104 chemical sciences ,Anti-Bacterial Agents ,chemistry ,Chemistry (miscellaneous) ,pruebas de sensibilidad microbiana ,Molecular Medicine ,antibacterianos ,Antibacterial activity ,Lead compound ,Bacteria ,Azo-compound ,Synthesis ,Nuclear chemistry - Abstract
Some novel (phenyl-diazenyl) phenols (4a-m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by H-1 nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC100 values of 4 mu g/mL and 8 mu g/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds., This research work was financially supported by the Italian Minister of Instruction, University and Research (MIUR)-300395FRB16. The authors are grateful to Fabrizio dal Piaz for the mass spectral measurements.
- Published
- 2017