Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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

Simona Concilio
* ORCID logo ,
Lucia Sessa
ORCID logo ,
Anna Maria Petrone
,
Amalia Porta
,
Rosita Diana
,
Pio Iannelli
,
Stefano Piotto
ORCID logo
Version 1 : Received: 5 May 2017 / Approved: 5 May 2017 / Online: 5 May 2017 (13:38:51 CEST)

A peer-reviewed article of this Preprint also exists.

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. 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.

Abstract

Some novel (phenyl-diazenyl)phenols (3a–g) 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 nuclear magnetic resonance (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.

Keywords

azo-compound; antimicrobial; synthesis; QSAR.

Subject

Chemistry and Materials Science, Theoretical Chemistry

Copyright: 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.

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