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. 2019 Apr:85:221-228.
doi: 10.1016/j.bioorg.2018.12.029. Epub 2018 Dec 21.

Synthesis, antioxidant and Aβ anti-aggregation properties of new ferulic, caffeic and lipoic acid derivatives obtained by the Ugi four-component reaction

Mohamed Benchekroun  1 , Irene Pachón-Angona  1 , Vincent Luzet  1 , Helene Martin  2 , María-Jesús Oset-Gasque  3 , José Marco-Contelles  4 , Lhassane Ismaili  5
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Synthesis, antioxidant and Aβ anti-aggregation properties of new ferulic, caffeic and lipoic acid derivatives obtained by the Ugi four-component reaction

Mohamed Benchekroun et al. Bioorg Chem. 2019 Apr.

Abstract

We report herein the synthesis antioxidant and Aβ anti-aggregation capacity of (E)-N-benzyl-N-[2-(benzylamino)-2-oxoethyl]-3-(aryl)acrylamides and related (R)-N-benzyl-N-(2-(benzylamino)-2-oxoethyl)-5-(1,2-dithiolan-3-yl)pentanamides 1-12. These compounds have been obtained, via Ugi four-component reaction, from modest to good yields. Their antioxidant analysis, using the DPPH and ORAC assays, allowed us to identify compounds 8 and 9, as potent antioxidant agents, showing also strong Aβ1-40 self-aggregation inhibition, two biological properties of interest in pathologies linked to the oxidative stress, such as Alzheimer's disease.

Keywords: (R)-Lipoic acid; Antioxidants; Aβ(1−40) self-aggregation inhibition; Benzyl isocyanide; Benzylamine; Caffeic acid; Ferulic acid; Multicomponent reactions; Ugi four-component reaction.

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