Synthesis and anti-inflammatory activity of isoquebecol.

Autor: Cardinal S; Département de Chimie and PROTEO, Université Laval, 1045 Avenue de la Médecine, Québec G1V 0A6, Canada., Paquet-Côté PA; Département de Chimie and PROTEO, Université Laval, 1045 Avenue de la Médecine, Québec G1V 0A6, Canada., Azelmat J; Groupe de Recherche en Écologie Buccale, Faculté de Médecine Dentaire, Université Laval, 2420 Rue de la Terrasse, Québec G1V 0A6, Canada., Bouchard C; Département de Chimie and PROTEO, Université Laval, 1045 Avenue de la Médecine, Québec G1V 0A6, Canada., Grenier D; Groupe de Recherche en Écologie Buccale, Faculté de Médecine Dentaire, Université Laval, 2420 Rue de la Terrasse, Québec G1V 0A6, Canada., Voyer N; Département de Chimie and PROTEO, Université Laval, 1045 Avenue de la Médecine, Québec G1V 0A6, Canada. Electronic address: normand.voyer@chm.ulaval.ca.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2017 Apr 01; Vol. 25 (7), pp. 2043-2056. Date of Electronic Publication: 2017 Feb 16.
DOI: 10.1016/j.bmc.2017.01.050
Abstrakt: We report here the synthesis of isoquebecol, an unprecedented constitutional isomer of quebecol, a polyphenolic compound discovered in maple syrup. The methodology used to prepare isoquebecol involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor, followed by a double Suzuki-Miyaura reaction. The anti-inflammatory activity of isoquebecol was studied on macrophage cells by monitoring its ability to inhibit LPS-induced IL-6 secretion. Results show that this new compound has an improved bioactivity over that of its natural isomer. Precursors and derivatives of quebecol, isoquebecol and model analog 2,3,3-triphenylpropanol were also prepared and tested in this study. Comparison between the three series of compounds led to establishing new SARs concerning the aryl ring substitution pattern on the triarylpropanol scaffold and substructure functionalization.
(Copyright © 2017 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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