Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams.
Org Biomol Chem
; 17(5): 1130-1140, 2019 01 31.
Article
em En
| MEDLINE
| ID: mdl-30633287
ABSTRACT
Synthesis of novel triazole fused iminocyclitol-δ-lactams is described. The synthetic sequence involves the intermolecular [3 + 2] cycloaddition reaction of five-membered iminocyclitol derived azides with diethylacetylene dicarboxylate followed by intramolecular lactamisation, decarboxylation/reduction and final deprotection. Compound 3 is found to be a selective inhibitor of α-glucosidase from baker's yeast while two other compounds (2 and 4) that possess an additional hydroxymethyl group in the triazole ring are selective against ß-galactosidase from E. coli. Docking studies suggest the significance of the lactam carbonyl group for effective binding of these inhibitors with the active sites through hydrogen bonding.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Triazóis
/
Desenho de Fármacos
/
Alfa-Glucosidases
/
Ciclitóis
/
Inibidores de Glicosídeo Hidrolases
/
Iminas
/
Lactamas
Tipo de estudo:
Health_economic_evaluation
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Índia