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Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility

McGuigan, Christopher, Blewett, Sally Ann, Siccardi, Dario, Erichsen, Jonathan Thor, Andrei, G., Snoek, R., De Clercq, E. and Blazarini, J. 2002. Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility. Antiviral Chemistry & Chemotherapy 13 (2) , pp. 91-99.

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Abstract

We have previously reported bicyclic furanopyrimidines as potent and selective inhibitors of varicella zoster virus (VZV) with subnanomolar activity for p-alkylphenyl substituted analogues. These compounds are highly lipophilic and of limited water solubility. In an effort to address this issue, and with a view to oral dosing, we have sought to enhance water solubility whilst retaining high antiviral potency and we herein report a novel series of p-alkyloxyphenyl compounds which contain a phenolic ether atom intended to boost hydrophilicity. We report the synthesis, characterisation and antiviral evaluation of this series and note the retention of extremely high antiviral potency, with EC50 values as low as 1 nanomolar.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Optometry and Vision Sciences
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords: VZV, furanopyrimidines, nucleosides
Publisher: International Medical Press
ISSN: 0956-3202
Last Modified: 20 Oct 2017 18:05
URI: http://orca.cf.ac.uk/id/eprint/18553

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