Systematic synthesis and biological evaluation of alpha- and beta-D-lyxofuranosyl nucleosides of the five naturally occurring nucleic acid bases.

Abstract:

:The alpha- and beta-D-lyxofuranosyl analogues of the naturally occurring nucleosides have been synthesized and their antiviral properties examined. The alpha anomers were prepared by glycosylation of purine and pyrimidine aglycons with tetra-O-acetyl-alpha-D-lyxofuranose, followed by removal of the blocking groups. The beta anomers were obtained by sequential oxidation and reduction of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-beta-D-x ylofuranosyl nucleosides. The lyxofuranosyl nucleosides were tested for their activity against a variety of RNA and DNA viruses and for inhibition of cell growth. One compound, 9-alpha-D-lyxofuranosyladenine, showed activity against herpes simplex virus types 1 and 2 both in vitro and in vivo.

journal_name

J Med Chem

authors

Gosselin G,Bergogne MC,De Rudder J,De Clercq E,Imbach JL

doi

10.1021/jm00389a005

subject

Has Abstract

pub_date

1987-06-01 00:00:00

pages

982-91

issue

6

eissn

0022-2623

issn

1520-4804

journal_volume

30

pub_type

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