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.
CEQOFFUP, Portugal.
Nuno
N
Milhazes
Rita
R
Calheiros
M Paula M
MP
Marques
Jorge
J
Garrido
M Natália D S
MN
Cordeiro
Cátia
C
Rodrigues
Sandra
S
Quinteira
Carla
C
Novais
Luísa
L
Peixe
Fernanda
F
Borges
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004563:Electrochemistry; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D013343:Styrenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
C512238:3-hydroxy-4-methoxy-beta-methyl-beta-nitrostyrene; D000900:Anti-Bacterial Agents; D013343:Styrenes; C011955:beta-nitrostyrene