72305-96-5Relevant articles and documents
PHOSPHONOFORMIC ACID ESTERS
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, (2008/06/13)
A compound of the formula, wherein R1, R2 and R3 are the same or different, and each is selected from the group consisting of hydrogen and phenyl groups of the formula, wherein R4 and R5 are the same or different and each is selected from the group consis
Synthesis of esters of phosphonoformic acid and their antiherpes activity
Noren,Helgstrand,Johansson,Misiorny,Stening
, p. 264 - 270 (2007/10/02)
Aliphatic and aromatic mono-, di-, and triesters of phosphonoformic (foscarnet) were synthesized. The triesters were prepared by the Michaelis-Arbuzov reaction and were hydrolyzed to di- and monoesters. The compounds were tested for antiviral activity on isolated herpes simplex virus type 1 (HSV-1) DNA polymerase, in a HSV-1 plaque reduction assay, and on a cutaneous HSV-1 infection in guinea pigs. None of the esters inhibited the activity of isolated HSV-1 polymerases. Monoesters with a free carboxylic group and diesters with an aromatic carboxylic ester function were active against the cutaneous herpesa infection. Mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with aliphatic carboxylic ester groups were inactive in all test systems. The results show that all three acidic groups of phosphonoformic acid must be free in order to get antiviral activity at the enzyme level. However, certain esters of this acid may be biotransformed to the acid itself to give antiherpes activity.