2-methoxy-4-[(E)-2-nitrovinyl]phenol

Potential antibacterial agent  against the Gram-positive bacteria (MIC = 256 mg/L)

OTAVAchemicals Catalogue Number:   0107930017

CAS Registry Number:  6178-42-3

Purity: 95%

Ref.: b-Nitrostyrene derivatives as potential antibacterial agents: A structure–property–activity relationship study. Milhazes, N., Calheiros, R., Marques, M. P. M., Garrido, J., Cordeiro, M. N. D. S., Rodrigues, C., Borges, F. Bioorg. Med. Chem., 2006, 14, 4078–4088.

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

DOI: 10.1016/j.bmc.2006.02.006