Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor

Carla Marino, P. Herczegh, Rosa M. De Lederkremer

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)123-128
Number of pages6
JournalCarbohydrate Research
Volume333
Issue number2
DOIs
Publication statusPublished - Jul 3 2001

Fingerprint

Thiones
Nucleosides
Ethylenethiourea
Imidazolines
Nucleophiles
Mammals
Pathogens
Biological Assay
Microorganisms
Assays
Derivatives
2-mercaptoimidazole
isothiocyanic acid

Keywords

  • 4-Imidazoline
  • Galactofuranosidase inhibitors
  • Imidazolidine-2-thion derivatives
  • Isothiocyanate
  • Thiohydantoin

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor. / Marino, Carla; Herczegh, P.; De Lederkremer, Rosa M.

In: Carbohydrate Research, Vol. 333, No. 2, 03.07.2001, p. 123-128.

Research output: Contribution to journalArticle

@article{18a8a576be564a188a068e896c458ba6,
title = "Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor",
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.",
keywords = "4-Imidazoline, Galactofuranosidase inhibitors, Imidazolidine-2-thion derivatives, Isothiocyanate, Thiohydantoin",
author = "Carla Marino and P. Herczegh and {De Lederkremer}, {Rosa M.}",
year = "2001",
month = "7",
day = "3",
doi = "10.1016/S0008-6215(01)00146-X",
language = "English",
volume = "333",
pages = "123--128",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "2",

}

TY - JOUR

T1 - Synthesis of β-D-galactofuranosyl nucleoside analogues. A new type of β-D-galactofuranosidase inhibitor

AU - Marino, Carla

AU - Herczegh, P.

AU - De Lederkremer, Rosa M.

PY - 2001/7/3

Y1 - 2001/7/3

N2 - 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.

AB - 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.

KW - 4-Imidazoline

KW - Galactofuranosidase inhibitors

KW - Imidazolidine-2-thion derivatives

KW - Isothiocyanate

KW - Thiohydantoin

UR - http://www.scopus.com/inward/record.url?scp=0035800135&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035800135&partnerID=8YFLogxK

U2 - 10.1016/S0008-6215(01)00146-X

DO - 10.1016/S0008-6215(01)00146-X

M3 - Article

VL - 333

SP - 123

EP - 128

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 2

ER -