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

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TitreSynthesis, antioxidant and A beta anti-aggregation properties of new ferulic, caffeic and lipoic acid derivatives obtained by the Ugi four-component reaction
Type de publicationJournal Article
Year of Publication2019
AuteursBenchekroun M, Pachon-Angona I, Luzet V, Martin H, Oset-Gasque M-J, Marco-Contelles J, Ismaili L
JournalBIOORGANIC CHEMISTRY
Volume85
Pagination221-228
Date PublishedAPR
Type of ArticleArticle
ISSN0045-2068
Mots-clés(R)-Lipoic acid, A beta(1-40) self-aggregation inhibition, antioxidants, Benzyl isocyanide, Benzylamine, Caffeic acid, Ferulic acid, multicomponent reactions, Ugi four-component reaction
Résumé

We report herein the synthesis antioxidant and A beta anti-aggregation capacity of (E)-N-benzyl-N-[2-(benzyla-mino)-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 A beta(1-40 )self-aggregation inhibition, two biological properties of interest in pathologies linked to the oxidative stress, such as Alzheimer's disease.

DOI10.1016/j.bioorg.2018.12.029