[Synthesis and antiherpes activity of acyclovir phosphoesters].
9-(Hydroxyethyloxymethyl)guanine (acyclovir) phosphite and fluorophosphate were synthesized by the reactions of acyclovir with phosphorus trichloride in triethyl phosphate and with fluorophosphoric acid in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride, respectively, and characterized by the data of 1H and 31P NMR and mass spectra. These products selectively inhibit reproduction of the herpes simplex virus type 1 in the Vero cell culture, the phosphite being also substantially active against a herpes virus strain resistant to acyclovir.
Galegov
G A
GA
Ivanovskii Institute of Virology, Russian Academy of Medical Sciences, Moscow, Russia.
Shobukhov
V M
VM
Leont'eva
N A
NA
Ias'ko
M V
MV
D000212:Acyclovir / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002712:Chlorides / Q000737:chemistry; D002522:Chlorocebus aethiops; D004351:Drug Resistance; D005459:Fluorides / Q000737:chemistry; D018259:Herpesvirus 1, Human / Q000187:drug effects* / Q000502:physiology; D010755:Organophosphates / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D017553:Phosphorus Compounds / Q000737:chemistry; D014709:Vero Cells; D014779:Virus Replication / Q000187:drug effects*
D000998:Antiviral Agents; D002712:Chlorides; D010755:Organophosphates; D010710:Phosphates; D017553:Phosphorus Compounds; C111023:acyclovir fluorophosphate; C111022:acyclovir phosphite; C012980:fluorophosphate; C043693:phosphorus chloride; D005459:Fluorides; C009549:triethyl phosphate; D000212:Acyclovir
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