Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants

S. T. Caldwell, R. C. Hartley, D. B. McPhail, G. G. Duthie

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy-and tetramethoxybenzoic acids accessed by lithiation-carboxylation reactions. Direct enolate acylation was preferred over Baker-Venkataraman rearrangement when there were methoxy groups at both the 2-and the 6-position of the benzoic acid derivatives.
Original languageEnglish
Pages (from-to)23-33
Number of pages11
JournalCanadian Journal of Chemistry
Volume90
Issue number1
DOIs
Publication statusPublished - Jan 2012

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Bearings (structural)
Carboxylation
Acylation
Flavonoids
Benzoic Acid
Benzoic acid
Vitamins
Antioxidants
Vitamin E
Derivatives
Membranes
Acids
myricetin

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Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants. / Caldwell, S. T.; Hartley, R. C.; McPhail, D. B.; Duthie, G. G.

In: Canadian Journal of Chemistry, Vol. 90, No. 1, 01.2012, p. 23-33.

Research output: Contribution to journalArticle

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