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Title: β-Nitrostyrene derivatives as potential antibacterial agents: A structure–property–activity relationship study
Authors: Milhazes, Nuno 
Calheiros, Rita 
Marques, M. Paula M. 
Garrido, Jorge 
Cordeiro, M. Natália D.S. 
Rodrigues, Cátia 
Quinteira, Sandra 
Novais, Carla 
Peixe, Luísa 
Borges, Fernanda 
Keywords: Anti-Bacterial Agents; Electrochemistry; Gram-Positive Bacteria; Microbial Sensitivity Tests; Models, Molecular; Molecular Structure; Oxidation-Reduction; Structure-Activity Relationship; Styrenes
Issue Date: 2006
Serial title, monograph or event: Bioorganic & Medicinal Chemistry
Volume: 14
Issue: 12
Abstract: A multidisciplinary project was developed, combining the synthesis of a series of beta-nitrostyrene derivatives and the determination of their physicochemical parameters (redox potentials, partition coefficients), to the evaluation of the corresponding antibacterial activity. A complete conformational analysis was also performed, in order to get relevant structural information. Subsequently, a structure-property-activity (SPAR) approach was applied, through linear regression analysis, aiming at obtaining a putative correlation between the physicochemical parameters of the compounds investigated and their antibacterial activity (both against standard strains and clinical isolates). The beta-nitrostyrene compounds displayed a lower activity towards all the tested bacteria relative to the beta-methyl-beta-nitrostyrene analogues. This was observed particularly for the 3-hydroxy-4-methoxy-beta-methyl-beta-nitrostyrene (IVb) against the Gram-positive bacteria (Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium). The SPAR results revealed the existence of a clear correlation between the redox potentials and the antibacterial activity of the series of beta-nitrostyrene derivatives under study.
Other Identifiers: 10.1016/j.bmc.2006.02.006
DOI: 10.1016/j.bmc.2006.02.006
Rights: openAccess
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais

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