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...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2009-09, Vol.44 (9), p.3830-3835
Main Authors: Sousa, Emília, Paiva, Ana, Nazareth, Nair, Gales, Luis, Damas, Ana M., Nascimento, Maria S.J., Pinto, Madalena
Format: Article
Language:English
Subjects:
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor
Biological and medical sciences
Bromoalkoxyxanthone
Cell Line, Tumor
Cell Proliferation - drug effects
Crystallography, X-Ray
General aspects
Humans
Inhibitory Concentration 50
Medical sciences
Models, Molecular
Molecular Structure
Oxygen heterocycle
Pharmacology. Drug treatments
X-ray diffraction
Xanthones
Xanthones - chemical synthesis
Xanthones - chemistry
Xanthones - pharmacology
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Summary: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)° with the 6-bromohexyl side chain. These results revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs. [Display omitted] The investigation of secondary products in the synthesis of dimeric xanthones revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2009.04.011