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- W654209102 abstract "While heterocyclic compounds have found early wide applications because if their broad spectrum of bioactivities, the development of Glycosciences has shown the importance of carbohydrates for Life, and the crucial roles they exert for the normal development of living organisms, or their control based on glycomimics. These reasons explain the topic of this thesis : SYNTHESIS OF GLYCOHETEROCYCLES AS INHIBITORS OF GLYCOGEN PHOSPHORYLASE AND PROTEIN KINASES. The first chapter describes 1,3-dipolar cycloadditions reactions between sugar-based acrylates and cinnamates and such dipoles as trimethylsilyldiazomethane and nitrile oxides. Modest stereoinductions were observed, which were enhanced by using chiral dipoles. Chapter 2 is devoted to cycloadditions between several nitrile oxides and exo-glucals, one hydroximo-lactone or benzoylated -D-glucopyranosyl cyanide. Chapter 3 concerns synthetic routes toward 3-C-glucosyl-1,2,4-oxadiazoles obtained when -D-glucopyranosyl cyanides were converted into amidoximes, then reacted by O-acylation followed by thermal cyclization. The prepared glycomimics were tested as glycogen phosphorylase (GP) and protein kinases (PK) inhibitors. The best GP inhibitor was a glucosyl-spiro-isoxazoline with a 2-naphthyl substituent (Ki : 630 nM). The 5-C-glucosyl-1,2,4-oxadiazoles were better inhibors of GP as compared to their 3-C-glucosyl analogs, as indicated by their Ki (respectively 2,4 and 26,2 M for molecules with a 2-naphthyl substituent). Some compounds inhibited also various PK" @default.
- W654209102 created "2016-06-24" @default.
- W654209102 creator A5024383954 @default.
- W654209102 date "2006-01-01" @default.
- W654209102 modified "2023-09-27" @default.
- W654209102 title "Synthèses de glyco-héterocycles inhibiteurs de la glycogène phosphorylase et de protéine kinases" @default.
- W654209102 hasPublicationYear "2006" @default.
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