The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-beta-D-(arabinofuranosyl)uracil phosphoramidate ProTides

Youcef Mehellou; Jan Balzarini; Christopher McGuigan

doi:10.3851/IMP1476

The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-beta-D-(arabinofuranosyl)uracil phosphoramidate ProTides

Youcef Mehellou, Jan Balzarini, Christopher McGuigan

Birmingham Medical School

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Nucleoside analogues always require phosphorylation to be active. This appears to be a particular limitation for uridine-based nucleosides. Our ProTide method allows the direct use of masked membrane-soluble preformed nucleoside phosphates, bypassing the need for the initial phosphorylation step. We herein applied it to some novel 5-trimethylsilyl arabinosyl uridines.

Original language	English
Pages (from-to)	153-60
Number of pages	8
Journal	Antiviral chemistry & chemotherapy
Volume	20
Issue number	4
DOIs	https://doi.org/10.3851/IMP1476
Publication status	Published - 2010

Keywords

Amides
Animals
Antiviral Agents
Arabinofuranosyluracil
Cell Line, Tumor
Cercopithecus aethiops
Cytopathogenic Effect, Viral
Dogs
Fibroblasts
Humans
Magnetic Resonance Spectroscopy
Models, Molecular
Phosphoric Acids
Trimethylsilyl Compounds
Virus Replication

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10.3851/IMP1476

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title = "The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-beta-D-(arabinofuranosyl)uracil phosphoramidate ProTides",

abstract = "Nucleoside analogues always require phosphorylation to be active. This appears to be a particular limitation for uridine-based nucleosides. Our ProTide method allows the direct use of masked membrane-soluble preformed nucleoside phosphates, bypassing the need for the initial phosphorylation step. We herein applied it to some novel 5-trimethylsilyl arabinosyl uridines.",

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author = "Youcef Mehellou and Jan Balzarini and Christopher McGuigan",

year = "2010",

doi = "10.3851/IMP1476",

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T1 - The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-beta-D-(arabinofuranosyl)uracil phosphoramidate ProTides

AU - Mehellou, Youcef

AU - Balzarini, Jan

AU - McGuigan, Christopher

PY - 2010

Y1 - 2010

N2 - Nucleoside analogues always require phosphorylation to be active. This appears to be a particular limitation for uridine-based nucleosides. Our ProTide method allows the direct use of masked membrane-soluble preformed nucleoside phosphates, bypassing the need for the initial phosphorylation step. We herein applied it to some novel 5-trimethylsilyl arabinosyl uridines.

AB - Nucleoside analogues always require phosphorylation to be active. This appears to be a particular limitation for uridine-based nucleosides. Our ProTide method allows the direct use of masked membrane-soluble preformed nucleoside phosphates, bypassing the need for the initial phosphorylation step. We herein applied it to some novel 5-trimethylsilyl arabinosyl uridines.

KW - Amides

KW - Animals

KW - Antiviral Agents

KW - Arabinofuranosyluracil

KW - Cell Line, Tumor

KW - Cercopithecus aethiops

KW - Cytopathogenic Effect, Viral

KW - Dogs

KW - Fibroblasts

KW - Humans

KW - Magnetic Resonance Spectroscopy

KW - Models, Molecular

KW - Phosphoric Acids

KW - Trimethylsilyl Compounds

KW - Virus Replication

U2 - 10.3851/IMP1476

DO - 10.3851/IMP1476

M3 - Article

C2 - 20231780

SN - 0956-3202

VL - 20

SP - 153

EP - 160

JO - Antiviral chemistry & chemotherapy

JF - Antiviral chemistry & chemotherapy

IS - 4

ER -

The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-beta-D-(arabinofuranosyl)uracil phosphoramidate ProTides

Abstract

Keywords

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