Pseudoamide-type pyrrolidine and pyrrolizidine glycomimetics and their inhibitory activities against glycosidases.
J Org Chem
; 69(10): 3578-81, 2004 May 14.
Article
em En
| MEDLINE
| ID: mdl-15132577
ABSTRACT
Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirrolidinas
/
Alcaloides de Pirrolizidina
/
Inibidores Enzimáticos
/
Amidas
/
Glicosídeo Hidrolases
Idioma:
En
Ano de publicação:
2004
Tipo de documento:
Article