Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase

Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidine...

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Detalles Bibliográficos
Publicado: 2005
Materias:
Galactofuranose
Galactofuranosidase inhibitors
Glycobiology
Heteroaryl 1-thio-β-D-galactofuranosides
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_14246376_v2005_n12_p341_Marino
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spelling paper:paper_14246376_v2005_n12_p341_Marino2023-06-08T16:13:57Z Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase Galactofuranose Galactofuranosidase inhibitors Glycobiology Heteroaryl 1-thio-β-D-galactofuranosides Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidinethiol were employed as thiols, as such heteroaromatic aglycons are expected to display particular interactions with the active site of the enzyme. These thiols were condensed with per-O-benzoyl-D-galactofuranose, in the presence of SnCl4 or BF3.OEt2, followed by O-debenzoylation under mild conditions to afford the heteroaryl 1-thio-β-D-galactofuranosides in high yields. The enzymatic assays showed that 4,6-dimethyl-2-pyrimidyl 1-thio-β-D-galactofuranoside was the best inhibitor (IC50 135 μM), considerable more potent than the analogue lacking the methyl groups in the aglycon moiety. © ARKAT USA, Inc. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Galactofuranose
Galactofuranosidase inhibitors
Glycobiology
Heteroaryl 1-thio-β-D-galactofuranosides
spellingShingle Galactofuranose
Galactofuranosidase inhibitors
Glycobiology
Heteroaryl 1-thio-β-D-galactofuranosides
Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
topic_facet Galactofuranose
Galactofuranosidase inhibitors
Glycobiology
Heteroaryl 1-thio-β-D-galactofuranosides
description Heteroaryl 1-thio-β-D-galactofuranosides have been synthesized and evaluated as inhibitors of the exo-β-D-galactofuranosidase from Penicillium fellutanum. 2-Pyridinethiol, 4-pyridinethiol, 1-methylimidazole-2-thiol, 5-methy1-1,3,4-thiadiazole-2-thiol, 2-pyrimidinethiol and 4,6-dimethyl-2- pyrimidinethiol were employed as thiols, as such heteroaromatic aglycons are expected to display particular interactions with the active site of the enzyme. These thiols were condensed with per-O-benzoyl-D-galactofuranose, in the presence of SnCl4 or BF3.OEt2, followed by O-debenzoylation under mild conditions to afford the heteroaryl 1-thio-β-D-galactofuranosides in high yields. The enzymatic assays showed that 4,6-dimethyl-2-pyrimidyl 1-thio-β-D-galactofuranoside was the best inhibitor (IC50 135 μM), considerable more potent than the analogue lacking the methyl groups in the aglycon moiety. © ARKAT USA, Inc.
title Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_short Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_full Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_fullStr Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_full_unstemmed Synthesis of heteroaryl 1-thio-β-D-galactofuranosides and evaluation of their inhibitory activity towards a β-D-galactofuranosidase
title_sort synthesis of heteroaryl 1-thio-β-d-galactofuranosides and evaluation of their inhibitory activity towards a β-d-galactofuranosidase
publishDate 2005
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p341_Marino
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p341_Marino
_version_ 1768546689007747072

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