Dihydroxyxanthones prenylated derivatives: Synthesis, structure elucidation, and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7

• Type: Article in International Scientific Journal
• Date: 2007

Authors

Raquel A.P. Castanheiro (Author) FFUP; Madalena M.M. Pinto (Author) FFUP; Artur M.S. Silva (Author) Other; Sara M.M. Cravo (Author) FFUP; Luís Gales (Author) Other; Ana M. Damas (Author) Other; Naïr Nazareth (Author) Other; Maria S.J. Nascimento (Author) FFUP; Graham Eaton (Author) Other

Journal

Title: Bioorganic and Medicinal Chemistry

Vol. 15 No. 18

Pages: 6080-6088

ISSN: 0968-0896

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 48 Citations

Scopus - 54 Citations

Pubmed / Medline

Scientific classification

FOS: Medical and Health sciences > Other medical sciences

CORDIS: Health sciences

Other information

Authenticus ID: P-004-7H0

Resumo (PT): The synthesis, structure elucidation, and antitumor activity of 11 xanthones are reported, being the compounds 3, 4, 6–8, and 9 described for the first time. Xanthones 1 and 2 were used as building blocks to obtain the prenylated derivatives 3–8. Prenylation was carried out using prenyl bromide in alkaline medium. Dihydropyranoxanthones 9–11 were obtained from compounds 4 and 5 by an oxidative ring closure. The structure of the compounds was established by IR, UV, MS, and NMR (1H, 13C, COSY, HSQC, and HMBC) techniques and for compounds 4, 6, and 11 the structure was confirmed by X-ray crystallographic analysis. The effect of the 11 xanthones on the in vitro growth of four human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), SF-268 (central nervous system cancer), and UACC-62 (melanoma) is also described. <br> <br> Keywords: Xanthones; Prenylation; Antitumor activity; X-ray crystallography; NMR spectroscopy <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4P1P6S9-2&_user=2460038&_coverDate=09%2F15%2F2007&_rdoc=11&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232007%23999849981%23663813%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=36&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=4a05c4dd06e9310de7646e2e9afc86a0&searchtype=a"> Texto integral</a> <br> <br>

Abstract (EN): The synthesis, structure elucidation, and antitumor activity of 11 xanthones are reported, being the compounds 3, 4, 6–8, and 9 described for the first time. Xanthones 1 and 2 were used as building blocks to obtain the prenylated derivatives 3–8. Prenylation was carried out using prenyl bromide in alkaline medium. Dihydropyranoxanthones 9–11 were obtained from compounds 4 and 5 by an oxidative ring closure. The structure of the compounds was established by IR, UV, MS, and NMR (1H, 13C, COSY, HSQC, and HMBC) techniques and for compounds 4, 6, and 11 the structure was confirmed by X-ray crystallographic analysis. The effect of the 11 xanthones on the in vitro growth of four human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), SF-268 (central nervous system cancer), and UACC-62 (melanoma) is also described. <br> <br> Keywords: Xanthones; Prenylation; Antitumor activity; X-ray crystallography; NMR spectroscopy <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4P1P6S9-2&_user=2460038&_coverDate=09%2F15%2F2007&_rdoc=11&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232007%23999849981%23663813%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=36&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=4a05c4dd06e9310de7646e2e9afc86a0&searchtype=a"> Full text </a> <br> <br>

Language: English

Type (Professor's evaluation): Scientific