Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

Andrew D. Briggs; Michel Camplo; Sally Freeman; Jan Lundström; Brian G. Pring

doi:10.1016/0040-4020(96)00906-4

Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

Andrew D. Briggs, Michel Camplo, Sally Freeman, Jan Lundström, Brian G. Pring

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

Abstract

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.

Original language	English
Pages (from-to)	14937-14950
Number of pages	13
Journal	Tetrahedron
Volume	52
Issue number	47
DOIs	https://doi.org/10.1016/0040-4020(96)00906-4
Publication status	Published - 18 Nov 1996

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title = "Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate",

abstract = "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.",

author = "Briggs, {Andrew D.} and Michel Camplo and Sally Freeman and Jan Lundstr{\"o}m and Pring, {Brian G.}",

year = "1996",

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T1 - Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

AU - Briggs, Andrew D.

AU - Camplo, Michel

AU - Freeman, Sally

AU - Lundström, Jan

AU - Pring, Brian G.

PY - 1996/11/18

Y1 - 1996/11/18

N2 - 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.

AB - 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.

U2 - 10.1016/0040-4020(96)00906-4

DO - 10.1016/0040-4020(96)00906-4

M3 - Article

SN - 0040-4020

VL - 52

SP - 14937

EP - 14950

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

Abstract

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