Neoglycorandomization and digitoxin analogs

Details Neoglycorandomization and digitoxin analogs Neoglycorandomization and digitoxin analogs

C - Chemistry, Metallurgy

07

J

C07J 41/00 (2006.01) A61K 31/58 (2006.01) A61P 35/00 (2006.01)

Patent

CA 2571409

The present invention provides methods of producing libraries of compounds with enhanced desirable properties and diminished side effects as well as the compounds produced by the methods. In preferred embodiments, methods of the present invention use a universal chemical glycosylation method that employs reducing sugars and requires no protection or activation. In a preferred embodiment, the invention provides a library of neoglycoside digitoxin analogs that includes compounds with significantly enhanced cytotoxic potency toward human cancer cells and tumor-specificity, but are less potent Na+/K+-ATPase inhibitors in a human cell line than digitoxin.

L'invention porte sur des procédés d'élaboration de bibliothèques de composés aux caractéristiques désirables améliorées et à effets secondaires réduits, ainsi que sur les composés ainsi sélectionnés. Dans les exécutions préférées, les procédés de l'invention recourent à une méthode universelle de glycosylation chimique utilisant des sucres réducteurs et ne nécessitant ni protection, ni activation. Dans une exécution préférée, l'invention porte sur une bibliothèque d'analogues de néoglycoside digitoxine comprenant des composés à pouvoir cytotoxique sensiblement amélioré vis-à-vis de cellules cancéreuses et à spécificité tumorale, mais à moindre pouvoir inhibiteur vis-à-vis de la Na+/K+-ATPase de lignées de cellules humaines que la digitoxine.

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