Synthesis of beta-D-galactofuranosyl nucleoside analogues. A new type of beta-D-galactofuranosidase inhibitor.
The development of beta-D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta-D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta-D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta-D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta-D-Galactofuranosyl-O-ethylthiourethane, N-beta-D-galactofuranosyl-4-oxoimidazolidine-2-thione, N-beta-D-galactofuranosyl-4-imidazoline-2-thione, and N-beta-D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta-D-galactofuranosidase inhibitor.
Marino
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C
CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, 1428 Buenos Aires, Argentina. cmarino@qo.fcen.uba.ar
Herczegh
P
P
de Lederkremer
R M
RM
D005697:Galactosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D010407:Penicillium / Q000737:chemistry / Q000201:enzymology; D013865:Thioglycosides / Q000737:chemistry; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
D005697:Galactosides; D009705:Nucleosides; D013865:Thioglycosides; D001616:beta-Galactosidase