SrasV1, Main, Exploration, bibRecord, 006396

Halophenyl furanopyrimidines as potent and selective anti-VZV agents

Identifieur interne : 006396 ( Main/Exploration ); précédent : 006395; suivant : 006397

Halophenyl furanopyrimidines as potent and selective anti-VZV agents

Auteurs : Christopher Mcguigan [Royaume-Uni] ; Alison Jukes [Royaume-Uni] ; Sally Blewett [Royaume-Uni] ; Hubert Barucki [Royaume-Uni] ; Jonathan T. Erichsen [Royaume-Uni] ; Graciella Andrei [Belgique] ; Robert Snoeck [Belgique] ; Erik De Clercq [Belgique] ; Jan Balzarini [Belgique]

Source :

Antiviral chemistry & chemotherapy [ 0956-3202 ] ; 2003.

RBID : Pascal:03-0438460

Descripteurs français

English descriptors

KwdEn :
- Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Antiviral Agents (toxicity), Bicyclic compound, Bridged Bicyclo Compounds, Heterocyclic (chemical synthesis), Bridged Bicyclo Compounds, Heterocyclic (pharmacology), Bridged Bicyclo Compounds, Heterocyclic (toxicity), Cells, Cultured (drug effects), Chemical synthesis, Furan derivatives, Furans (chemistry), Halogen compound, Halogens (chemistry), Herpesvirus 3, Human (drug effects), Humans, Inhibitory Concentration 50, Magnetic Resonance Spectroscopy, Pyrimidine Nucleosides (chemical synthesis), Pyrimidine Nucleosides (pharmacology), Pyrimidine Nucleosides (toxicity), Pyrimidine nucleoside, Structure activity relation, Structure-Activity Relationship, Varicella zoster virus.
MESH :
- chemical , chemical synthesis : Antiviral Agents, Bridged Bicyclo Compounds, Heterocyclic, Pyrimidine Nucleosides.
- chemical , chemistry : Furans, Halogens.
- chemical , pharmacology : Antiviral Agents, Bridged Bicyclo Compounds, Heterocyclic, Pyrimidine Nucleosides.
- chemical , toxicity : Antiviral Agents, Bridged Bicyclo Compounds, Heterocyclic, Pyrimidine Nucleosides.
- drug effects : Cells, Cultured, Herpesvirus 3, Human.
- Humans, Inhibitory Concentration 50, Magnetic Resonance Spectroscopy, Structure-Activity Relationship.

Abstract

Bicyclic furano pyrimidines have been previously reported by us to be highly potent and selective inhibitors of varicella zoster virus (VZV). p-Alkyl phenyl analogues are particularly potent with EC₅₀ values below 1nM. In this article we report the synthesis and anti-VZV activity of a series of halophenyl analogues, with variation in the nature (F, Cl, Br) and location (o, m, p) of the halogen substituent. The compounds show a range of activities from ca. 10 nM to >50 μM. In most cases, ortho substitution leads to greatest activity, meta substitution is in general poor, and the effect of p-substitution shows a marked dependence on the halogen atom. The p-fluorophenyl compound is unique amongst compounds of this class in being inactive as an antiviral. The possible origins of these marked SARs are discussed.

Affiliations:

Le document en format XML

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<front><div type="abstract" xml:lang="en">Bicyclic furano pyrimidines have been previously reported by us to be highly potent and selective inhibitors of varicella zoster virus (VZV). p-Alkyl phenyl analogues are particularly potent with EC<sub>50</sub>
 values below 1nM. In this article we report the synthesis and anti-VZV activity of a series of halophenyl analogues, with variation in the nature (F, Cl, Br) and location (o, m, p) of the halogen substituent. The compounds show a range of activities from ca. 10 nM to >50 μM. In most cases, ortho substitution leads to greatest activity, meta substitution is in general poor, and the effect of p-substitution shows a marked dependence on the halogen atom. The p-fluorophenyl compound is unique amongst compounds of this class in being inactive as an antiviral. The possible origins of these marked SARs are discussed.</div>
</front>
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   |texte=   Halophenyl furanopyrimidines as potent and selective anti-VZV agents
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Halophenyl furanopyrimidines as potent and selective anti-VZV agents

Halophenyl furanopyrimidines as potent and selective anti-VZV agents

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