Synthesis of polyhydroxylated piperidines and evaluation as glycosidase inhibitors.

Tite, Tony; Lallemand, Marie-Christine; Poupon, Erwan; Kunesch, Nicole; Tillequin, François; Gravier-Pelletier, Christine; Le Merrer, Yves; Husson, Henri-Philippe

Tite, Tony; Lallemand, Marie-Christine; Poupon, Erwan; Kunesch, Nicole; Tillequin, François; Gravier-Pelletier, Christine; Le Merrer, Yves; Husson, Henri-Philippe.

Affiliation

Tite T; Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, UMR 8638 associée au CNRS et à l'Université René Descartes, 4, Avenue de l'Observatoire, 75270 Paris Cedex 06, France.

Bioorg Med Chem ; 12(19): 5091-7, 2004 Oct 01.

Article in En | MEDLINE | ID: mdl-15351392

ABSTRACT

ABSTRACT

A series of 16 new chiral nonracemic polyhydroxylated piperidines was synthesized utilizing several chiral beta-amino-alcohols. They act as a nitrogen source, chirality inducer and iminium stabilizer, in the desymmetrization of meso-trihydroxylated glutaraldehyde. The biological activity of these compounds towards several glycosidases (alpha-D-glucosidase, alpha-D-mannosidase, alpha-L-fucosidase) has been evaluated.

Subject(s)

Glycoside Hydrolases/antagonists & inhibitors; Piperidines/chemical synthesis; Bacterial Proteins/antagonists & inhibitors; Enzyme Inhibitors/chemical synthesis; Enzyme Inhibitors/pharmacology; Geobacillus stearothermophilus/chemistry; Piperidines/pharmacology; Structure-Activity Relationship; alpha-L-Fucosidase/antagonists & inhibitors; alpha-Mannosidase/antagonists & inhibitors

Search on Google

Add to My VHL

XML

PubMed Links

Collection: 01-internacional Database: MEDLINE Main subject: Piperidines / Glycoside Hydrolases Language: En Journal: Bioorg Med Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2004 Document type: Article Affiliation country: France Publication country: ENGLAND / ESCOCIA / GB / GREAT BRITAIN / INGLATERRA / REINO UNIDO / SCOTLAND / UK / UNITED KINGDOM

Search on Google

Add to My VHL

XML

PubMed Links