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Abstract:

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.

Registro:

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

Referencias:

  • Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552
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  • Marino, C., Mariño, K., Miletti, L., Manso Alves, M.J., Colli, W., Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904
  • Miletti, L., Marino, C., Mariño, K., Lederkremer, R.M., Colli, W., Manso Alves, M.J., (1999) Carbohydr. Res., 320, pp. 176-182
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  • Chiocconi, A., Marino, C., Lederkremer, R.M., (2000) Carbohydr. Res., 323, pp. 7-13
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Citas:

---------- APA ----------
Marino, C., Herczegh, P. & De Lederkremer, R.M. (2001) . Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor. Carbohydrate Research, 333(2), 123-128.
http://dx.doi.org/10.1016/S0008-6215(01)00146-X
---------- CHICAGO ----------
Marino, C., Herczegh, P., De Lederkremer, R.M. "Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor" . Carbohydrate Research 333, no. 2 (2001) : 123-128.
http://dx.doi.org/10.1016/S0008-6215(01)00146-X
---------- MLA ----------
Marino, C., Herczegh, P., De Lederkremer, R.M. "Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor" . Carbohydrate Research, vol. 333, no. 2, 2001, pp. 123-128.
http://dx.doi.org/10.1016/S0008-6215(01)00146-X
---------- VANCOUVER ----------
Marino, C., Herczegh, P., De Lederkremer, R.M. Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor. Carbohydr. Res. 2001;333(2):123-128.
http://dx.doi.org/10.1016/S0008-6215(01)00146-X