Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
In a study involving the synthesis of bis-intercalators, a bisxanthone and a minor product, 1-(6-bromohexyloxy)-xanthone were obtained. Although no capacity to inhibit the growth of human tumor cell lines was observed for the bisxanthone, the bromoalkoxyxanthone revealed this biological activity. In light of these results bromoalkylation of 3,4-dihydroxyxanthone furnished two bromohexyloxyxanthones that were investigated for their effect on the in vitro growth of human tumor cell lines MCF-7 (ER+, breast), MDA-MB-231 (ER-, breast), NCI-H460 (non-small lung), and SF-268 (central nervous system). The X-ray structure of 1-(6-bromohexyloxy)-xanthone revealed that the xanthone skeleton remains essentially planar forming a dihedral angle of 61.3(2) degrees with the 6-bromohexyl side chain. These results revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs.
Laboratório de Química Orgânica, Centro de Estudos Química Medicinal da Universidade do Porto, Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha, 164, 4050-047 Porto, Portugal. esousa@ff.up.pt
Emília
E
Sousa
Ana
A
Paiva
Nair
N
Nazareth
Luis
L
Gales
Ana M
AM
Damas
Maria S J
MS
Nascimento
Madalena
M
Pinto
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D015394:Molecular Structure; D044004:Xanthones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D044004:Xanthones; C009689:xanthone