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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2006

Autores

Nuno Milhazes (Autor) Outra; Rita Calheiros (Autor) Outra; M. Paula M. Marques (Autor) Outra; Jorge Garrido (Autor) Outra; M. Natália D.S. Cordeiro (Autor) Outra; Cátia Rodrigues (Autor) Outra; Sandra Quinteira (Autor) Outra; Carla Novais (Autor) Outra; Luísa Peixe (Autor) FFUP; Fernanda Borges (Autor) FFUP

Revista

Título: Bioorganic and Medicinal Chemistry

Vol. 14 Nº 12

Páginas: 4078-4088

ISSN: 0968-0896

Editora: Elsevier

Indexação

ISI Web of Science

Classificação Científica

FOS: Ciências médicas e da saúde > Outras ciências médicas

CORDIS: Ciências da Saúde

Outras Informações

Resumo (PT): 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. <br> <br> Keywords: β-Nitrostyrene derivatives; Antibacterial activity; Redox potentials; Structure–property–activity relationship <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4JB9MS4-1&_user=2460038&_coverDate=06%2F15%2F2006&_rdoc=11&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232006%23999859987%23622124%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=32&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=143d987c148985767510dbaf4f872cce&searchtype=a"> Texto integral</a> <br> <br>

Abstract (EN): 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. <br> <br> Keywords: β-Nitrostyrene derivatives; Antibacterial activity; Redox potentials; Structure–property–activity relationship <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4JB9MS4-1&_user=2460038&_coverDate=06%2F15%2F2006&_rdoc=11&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232006%23999859987%23622124%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=32&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=143d987c148985767510dbaf4f872cce&searchtype=a"> Full text </a> <br> <br>

Idioma: Inglês

Tipo (Avaliação Docente): Científica