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Milhazes, N. et al.

beta-Nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study.

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.[1]

References

beta-Nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study. Milhazes, N., Calheiros, R., Marques, M.P., Garrido, J., Cordeiro, M.N., Rodrigues, C., Quinteira, S., Novais, C., Peixe, L., Borges, F. Bioorg. Med. Chem. (2006) [Pubmed]

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