Imidazole analogues of resveratrol: synthesis and cancer cell growth evaluation

TETRAHEDRON

卷:71

Article

Bellina, Fabio¹  Guazzelli, Nicola¹  Lessi, Marco¹  Manzini, Chiara¹ 

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56124 Pisa, Italy

关键词: Cross-coupling;    Imidazoles;    Resveratrol;    Arylation;    Palladium catalyst;    Regioselectivity;    Bioactive compounds;    Anticancer compounds;   

DOI  :  10.1016/j.tet.2015.02.024

来源: Elsevier

【 摘 要 】

Novel trans-restricted analogues of resveratrol in which the C-C double bond of the natural derivative has been replaced by diaryl substituted imidazole analogues have been designed.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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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