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Molecules 2017, 22(6), 875; doi:10.3390/molecules22060875

Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds

Department of Industrial Engineering, University of Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Italy
Department of Pharmacy, University of Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Italy
PhD Program in Drug Discovery and Development, University of Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Italy
Department of Chemical Science, University of Napoli “Federico II”, Cupa Nuova Cintia 21, 80126 Napoli, Italy
Author to whom correspondence should be addressed.
Academic Editors: Krasimir Vasilev, Alex Cavallaro and Peter Zilm
Received: 4 May 2017 / Revised: 19 May 2017 / Accepted: 22 May 2017 / Published: 25 May 2017
(This article belongs to the Special Issue Antibacterial Materials and Coatings)
View Full-Text   |   Download PDF [1209 KB, uploaded 25 May 2017]   |  


Some novel (phenyl-diazenyl)phenols 3ag were designed and synthesized to be evaluated for their antimicrobial activity. A previously synthesized molecule, active against bacteria and fungi, was used as lead for modifications and optimization of the structure, by introduction/removal or displacement of hydroxyl groups on the azobenzene rings. The aim of this work was to evaluate the consequent changes of the antimicrobial activity and to validate the hypothesis that, for these compounds, a plausible mechanism could involve an interaction with protein receptors, rather than an interaction with membrane. All newly synthesized compounds were analyzed by 1H-NMR, DSC thermal analysis and UV-Vis spectroscopy. The in vitro minimal inhibitory concentrations (MIC) of each compound was determined against Gram-positive and Gram-negative bacteria and Candida albicans. Compounds 3b and 3g showed the highest activity against S. aureus and C. albicans, with remarkable MIC values of 10 µg/mL and 3 µg/mL, respectively. Structure-activity relationship studies were capable to rationalize the effect of different substitutions on the phenyl ring of the azobenzene on antimicrobial activity. View Full-Text
Keywords: azo-compound; antimicrobial; synthesis; QSAR azo-compound; antimicrobial; synthesis; QSAR

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Concilio, S.; Sessa, L.; Petrone, A.M.; Porta, A.; Diana, R.; Iannelli, P.; Piotto, S. Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds. Molecules 2017, 22, 875.

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