Dihydroxyxanthones prenylated derivatives: synthesis, structure elucidation, and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7.
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 ((1)H, (13)C, 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.
Castanheiro
Raquel A P
RA
Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia, Universidade do Porto, Portugal.
Pinto
Madalena M M
MM
Silva
Artur M S
AM
Cravo
Sara M M
SM
Gales
Luís
L
Damas
Ana M
AM
Nazareth
Naïr
N
Nascimento
Maria S J
MS
Eaton
Graham
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000970:Antineoplastic Agents; D044004:Xanthones