The development of β-D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because β-D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared β-D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated β-D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-β-D-Galactofuranosyl-O-ethylthiourethane, N-β-D-galactofuranosyl-4-oxoimidazolidine-2-thione, N-β-D-galactofuranosyl-4-imidazoline-2-thione, and N-β-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 β-D-galactofuranosidase inhibitor. © 2001 Elsevier Science Ltd.
Documento: | Artículo |
Título: | Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor |
Autor: | Marino, C.; Herczegh, P.; De Lederkremer, R.M. |
Filiación: | Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Universidad De Buenos Aires, 1428 Buenos Aires, Argentina Research Group for Chemistry of Antibiotics of the Hungarian Academy of Sciences, Faculty of Pharmaceutical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary |
Palabras clave: | 4-Imidazoline; Galactofuranosidase inhibitors; Imidazolidine-2-thion derivatives; Isothiocyanate; Thiohydantoin; Bioassay; Chemotherapy; Enzyme inhibition; Microorganisms; Synthesis (chemical); Nucleophiles; Carbohydrates; 1,3 diaza 1 beta dextro galactofuranosyl 2 thione; beta dextro galactofuranosidase; beta dextro galactofuranosidase inhibitor; beta dextro galactofuranosyl isothiocyanate; carbohydrate derivative; dextro galactono 1,4 lactone; enzyme inhibitor; fungal enzyme; imidazolidine derivative; imidazoline derivative; isothiocyanic acid derivative; ketone derivative; n beta dextro galactofuranosyl 4 imidazoline 2 thione; n beta dextro galactofuranosyl 4 methoxyimidazoline 2 thione; n beta dextro galactofuranosyl 4 oxoimidazolidine 2 thione; n beta dextro galactofuranosyl o ethylthiourethane; unclassified drug; article; chemical reaction; drug screening; drug structure; drug synthesis; enzyme activity; enzyme inhibition; priority journal; structure activity relation; beta-Galactosidase; Galactosides; Humans; Molecular Structure; Nucleosides; Penicillium; Thioglycosides; Mammalia |
Año: | 2001 |
Volumen: | 333 |
Número: | 2 |
Página de inicio: | 123 |
Página de fin: | 128 |
DOI: | http://dx.doi.org/10.1016/S0008-6215(01)00146-X |
Título revista: | Carbohydrate Research |
Título revista abreviado: | Carbohydr. Res. |
ISSN: | 00086215 |
CODEN: | CRBRA |
CAS: | beta-Galactosidase, EC 3.2.1.23; Galactosides; Nucleosides; Thioglycosides |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v333_n2_p123_Marino |