Synthesis and biological evaluation of guanidine-type iminosugars.
The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose --> piperidine rearrangement of 5-deoxy-5-guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.
Aguilar
Matilde
M
Departamento de Química OrgAnica, Facultad de Química, Universidad de Sevilla, Profesor García GonzAlez 1, E-41012 Sevilla, Spain.
Díaz-Pérez
Paula
P
García-Moreno
M Isabel
MI
Mellet
Carmen Ortiz
CO
García Fernandez
José M
JM
D004353:Drug Evaluation, Preclinical; D019791:Guanidine / Q000138:chemical synthesis* / Q000494:pharmacology*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment
D050111:Imino Sugars; D019791:Guanidine