Synthesis and anti-herpes simplex activity of analogues of phosphonoacetic acid.
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.
D000085:Acetates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D004259:DNA-Directed DNA Polymerase / Q000378:metabolism; D003864:Depression, Chemical; D003872:Dermatitis / Q000188:drug therapy; D005260:Female; D006561:Herpes Simplex / Q000188:drug therapy*; D051379:Mice; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use
D000085:Acetates; D000998:Antiviral Agents; D009943:Organophosphorus Compounds; D004259:DNA-Directed DNA Polymerase