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Synthesis and anti-herpes simplex activity of analogues of phosphonoacetic acid.

Synthesis and anti-herpes simplex activity of analogues of phosphonoacetic acid.

Authors :
Herrin TR
Fairgrieve JS
Bower RR
Shipkowitz NL
Source :
Journal of medicinal chemistry [J Med Chem] 1977 May; Vol. 20 (5), pp. 660-3.
Publication Year :
1977

Abstract

The synthesis of monoesters (P and C) of phosphonoacetic acid (PA) is given. The carboxyl esters were prepared by two methods: the reaction of chloroacetates with tris(trimethylsilyl) phosphite, followed by hydrolysis; and by the acid-catalyzed esterification of PA with the appropriate alcohol. P-Monoesters of PA were prepared either by the reaction of alkyl[bis(trimethylsilyl)] phosphite with benzyl chloroacetate followed by deprotection or by the reaction of dimethylphenyl phosphite with benzyl bromoacetate followed by hydrogenolysis. Three aryl- (alkyl-)phosphinic acid derivatives are reported. The above compounds were evaluated for anti-herpes activity against HSV-induced DNA polymerase and in animals infected with herpes dermatitis.

Details

Language :
English
ISSN :
0022-2623
Volume :
20
Issue :
5
Database :
MEDLINE
Journal :
Journal of medicinal chemistry
Publication Type :
Academic Journal
Accession number :
853505
Full Text :
https://doi.org/10.1021/jm00215a008