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Synthesis and anti-inflammatory activity of isoquebecol.

Abstract：

: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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Cardinal S,Paquet-Côté PA,Azelmat J,Bouchard C,Grenier D,Voyer N

doi

10.1016/j.bmc.2017.01.050

subject

Has Abstract

pub_date

2017-04-01 00:00:00

pages

2043-2056

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)30940-3

journal_volume

25

pub_type

杂志文章

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