Synthesis and antiviral activity of acyclovir-5 '-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug

Authors
McGuigan, C Slater, MJ Parry, NR Perry, A Harris, S
Citation
C. Mcguigan et al., Synthesis and antiviral activity of acyclovir-5 '-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug, BIOORG MED, 10(7), 2000, pp. 645-647
Citations number
17
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
7
Year of publication
2000
Pages
645 - 647
Database
ISI
SICI code
0960-894X(20000403)10:7<645:SAAAOA>2.0.ZU;2-5
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 a ctivities of this derivative against a range of viruses indicated poor intr acellular phosphate delivery, in marked contrast to the earlier successful delivery of several dideoxy anti-HIV nucleotides. (C) 2000 Elsevier Science Ltd. All rights reserved.