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

• Type: Article in International Scientific Journal
• Date: 2006

Authors

Milhazes, N (Author) Other; Calheiros, R (Author) Other; Marques, MPM (Author) Other; Garrido, J (Author) Other; Cordeiro, MNDS (Author) FCUP; Rodrigues, C (Author) Other; Quinteira, S (Author) Other; Novais, C (Author) FFUP; Peixe, L (Author) FFUP; Borges, F (Author) FFUP

Journal

Title: Bioorganic and Medicinal Chemistry

Vol. 14

Pages: 4078-4088

ISSN: 0968-0896

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 73 Citations

Scopus - 80 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-004-K5W

DOI: 10.1016/j.bmc.2006.02.006

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific