Design, synthesis and characterization of ferrocene containing aromatic foldamers & synthesis and study of novel indole based chalcones for anti-cancer activities

Liu, Yazhou
(2020)

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Authors
  • Liu, YazhouUCLouvain
    author
Supervisors
Singleton, Michael
;
Frédérick, Raphaël
Abstract
Part A Bent β-sheets play key roles in the active sites of many proteins. However, examples of AOFs mimicking sheet-like structures are rare. Among them, most reported structures have relied on rather rigid turn-units and, in some cases, the distance initially enforced between the strands is not ideal for good -stacking. To this end, we were curious if ferrocene, a flexional moiety containing ideal distance for -stacking, could be a suitable turn-unit for AOF β-sheet mimics. By incorporating ferrocene into aromatic oligoamides we successfully obtained a series of ferrocene containing AOFs. Through combined NMR, X-ray and computational studies, we revealed that for one of the series of oligomers, we can obtain a good preference for stacked sheet-like structures that show sequence dependent guest recognition and one other oligomer showed a stablized sheet-like conformation both in solid and solution based on the H-bonding network. Part B Chalcones have been shown to exhibit a variety of biological activities. Among these molecules, a new series of indole hybrid chalcones have drawn great attention for their novel biological activities. Our group has developed a novel methodology which allowed facile construction of indole-2-aldehydes though 2-acetylaniline and dichloroethylene. Based on these, a series of indole based chalcones with various modifications were obtained. Biological evaluation of these molecules demonstrated their potential anti-proliferative values in cancer cells.
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Citations

Liu, Y. (2020). Design, synthesis and characterization of ferrocene containing aromatic foldamers & synthesis and study of novel indole based chalcones for anti-cancer activities. https://hdl.handle.net/2078.5/104438