Structure modification of an active azo-compound as a route to new antimicrobial compounds
| Autor: | Stefano Piotto, Anna Maria Petrone, Rosita Diana, Amalia Porta, Pio Iannelli, Simona Concilio, Lucia Sessa |
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| Přispěvatelé: | Concilio, S., Sessa, L., Petrone, A. M., Porta, A., Diana, R., Iannelli, P., Piotto, S. |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Anti-Infective Agent
Quantitative structure–activity relationship azo-compound antimicrobial synthesis QSAR Stereochemistry Pharmaceutical Science Quantitative Structure-Activity Relationship 02 engineering and technology Microbial Sensitivity Tests 010402 general chemistry 01 natural sciences Article Azo Compound Analytical Chemistry lcsh:QD241-441 Antimicrobial Azo-compound Synthesis Medicine (all) Organic Chemistry chemistry.chemical_compound lcsh:Organic chemistry Anti-Infective Agents Drug Discovery Phenols Physical and Theoretical Chemistry Candida albicans Azo compound biology Bacteria Molecular Structure Microbial Sensitivity Test Chemistry Synthesi Fungi 021001 nanoscience & nanotechnology biology.organism_classification Combinatorial chemistry Corpus albicans 0104 chemical sciences Azobenzene Chemistry (miscellaneous) Molecular Medicine 0210 nano-technology Azo Compounds general_theoretical_chemistry |
| Zdroj: | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules, Vol 22, Iss 6, p 875 (2017) Molecules; Volume 22; Issue 6; Pages: 875 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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