Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
Sousa E, Paiva A, Nazareth N, Gales L, Damas AM, Nascimento MS, Pinto M.
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.