Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

Sodium pivaloyloxymethyl (pivaloyloxymethoxycarbonyl)phosphonate 4, sodium 4-acyloxybenzyl phenoxycarbonylphosphonates 14a-c and sodium 4-acyloxybenzyl benzyloxycarbonylphosphonates 15a,b have been prepared as bioreversible prodrugs of the antiviral phosphonoformate 1. Their hydrolyses, in vivo syst...

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Bibliographic Details
Published in:Tetrahedron 1996-11, Vol.52 (47), p.14937-14950
Main Authors: Briggs, Andrew D., Camplo, Michel, Freeman, Sally, Lundström, Jan, Pring, Brian G.
Format: Article
Language:English
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Summary:Sodium pivaloyloxymethyl (pivaloyloxymethoxycarbonyl)phosphonate 4, sodium 4-acyloxybenzyl phenoxycarbonylphosphonates 14a-c and sodium 4-acyloxybenzyl benzyloxycarbonylphosphonates 15a,b have been prepared as bioreversible prodrugs of the antiviral phosphonoformate 1. Their hydrolyses, in vivo systemic bioavailability and antiviral activity are reported. Of the compounds evaluated 4 was the best prodrug. Compounds 4, 14 and 15 have been prepared and evaluated as prodrugs of the antiviral phosphonoformate.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00906-4