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Halophenyl furanopyrimidines as potent and selective anti-VZV agents

McGuigan, Christopher ORCID: https://orcid.org/0000-0001-8409-710X, Jukes, Alison, Blewett, Sally, Barucki, Hubert, Erichsen, Jonathan T., Andrei, Graciella, Snoeck, Robert, De Clercq, Erik and Balzarini, Jan 2003. Halophenyl furanopyrimidines as potent and selective anti-VZV agents. Antiviral Chemistry and Chemotherapy 14 (3) , pp. 165-170.

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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 psubstitution 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Optometry and Vision Sciences
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RE Ophthalmology
R Medicine > R Medicine (General)
R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: VZV ; Bicyclic furano pyrimidines ; SARs
Publisher: International Medical Press
ISSN: 0956-3202
Last Modified: 17 Oct 2022 09:40
URI: https://orca.cardiff.ac.uk/id/eprint/5150

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