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

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.

• Authors: T R Herrin, J S Fairgrieve, R R Bower, N L Shipkowitz
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 20 Issue 5 Pg. 660-3 (May 1977) ISSN: 0022-2623 [Print] United States
• PMID: 853505 (Publication Type: Journal Article)

Chemical References

• Acetates
• Antiviral Agents
• Organophosphorus Compounds
• DNA-Directed DNA Polymerase

Topics

• Acetates (chemical synthesis, pharmacology, therapeutic use)
• Animals
• Antiviral Agents (chemical synthesis, therapeutic use)
• DNA-Directed DNA Polymerase (metabolism)
• Depression, Chemical
• Dermatitis (drug therapy)
• Female
• Herpes Simplex (drug therapy)
• Mice
• Organophosphorus Compounds (chemical synthesis, pharmacology, therapeutic use)