Imidazole analogues of resveratrol: synthesis and cancer cell growth evaluation. Issue 15 (15th April 2015)

• Record Type: Journal Article
• Authors: Bellina, Fabio; Guazzelli, Nicola; Lessi, Marco; Manzini, Chiara
• Is Part Of: Tetrahedron. Volume 71:Issue 15(2015)
• Page Start: 2298
• Page End: 2305
• Publication Date: 2015-04-15
• Subjects: Cross-coupling -- Imidazoles -- Resveratrol -- Arylation -- Palladium catalyst -- Regioselectivity -- Bioactive compounds -- Anticancer compounds; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.02.024
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Novel trans-restricted analogues of resveratrol in which the C–C double bond of the natural derivative has been replaced by diaryl substituted imidazole analogues have been designed. The syntheses of 1, 4-, 2, 4-, and 2, 5-diarylimidazoles, in which the two aryl moieties are linked to the heteroaromatic core in a 1, 3 fashion in order to preserve the trans stereochemistry, have been successfully carried out by regioselective sequential transition metal-catalyzed arylations of simple, commercially available imidazole precursors. The anticancer activity of selected analogues has been evaluated in vitro against the NCI-60 human tumor cell lines panel. From this screening, we were able to select a synthetic candidate that resulted more active than its natural lead. Graphical abstract: