title: Synthesis and antiviral activity of acyclovir-5'-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug.
abstract: We describe a synthesis of acyclovir-5'-(phenyl methoxy alaninyl) phosphate (2) from acyclovir (1). This compound was designed to act as a lipophilic, membrane-soluble prodrug of the free nucleotide. However, the biological activities of this derivative against a range of viruses indicated poor intracellular phosphate delivery, in marked contrast to the earlier successful delivery of several dideoxy anti-HIV nucleotides.
authors.affiliation: Welsh School of Pharmacy, Cardiff University, UK. mcguigan@cardiff.ac.uk
authors.forename: C
authors.initials: C
authors.lastname: McGuigan
authors.forename: M J
authors.initials: MJ
authors.lastname: Slater
authors.forename: N R
authors.initials: NR
authors.lastname: Parry
authors.forename: A
authors.initials: A
authors.lastname: Perry
authors.forename: S
authors.initials: S
authors.lastname: Harris
mesh_terms: D000212:Acyclovir / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002522:Chlorocebus aethiops; D003587:Cytomegalovirus / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects*; D014645:Herpesvirus 3, Human / Q000187:drug effects; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D012995:Solubility; D014709:Vero Cells
chemical_list: D000998:Antiviral Agents; D011355:Prodrugs; C412029:acyclovir-5'-(phenyl methoxy alaninyl)phosphate; D000212:Acyclovir