β-Nitrostyrene derivatives as potential antibacterial agents: A structure–property–activity relationship study

A multidisciplinary project was developed, combining the synthesis of a series of β-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 β-nitrostyrene compounds displayed a lower activity towards all the tested bacteria relative to the β-methyl-β-nitrostyrene analogues. This was observed particularly for the 3-hydroxy-4-methoxy-β-methyl-β-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 β-nitrostyrene derivatives under study.

An interactive study was developed combining the synthesis of a series of β-nitrostyrene and β-methyl-β-nitrostyrene derivatives and the evaluation of their antibacterial profile, along with the simultaneous determination of some physicochemical parameters, namely their conformational behaviour, redox potential and lipophilicity.Figure optionsDownload as PowerPoint slide