Synthesis and antiviral activity of 5'-deoxypyrazofurin.
In searching for derivatives of pyrazofurin that could display antiviral properties by means that do not require C-5' phosphorylation, 5'-deoxypyrazofurin (3) has been synthesized in six steps from methyl5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside (4). Compound 3 was evaluated for antiviral activity against a large number of viruses including herpes-, pox-, myxo-, toga-, arena-, rhabdo-, picorna-,reo-, and retroviruses. Compound 3 proved active against respiratory syncytial virus (in HeLa cells), vaccinia virus (in embryonic skin-muscle fibroblast cells), vesicular stomatitis virus (in HeLa cells), and influenza A virus (in Madin-Darby canine kidney cells) at concentrations (ranging from 4 to 20 micrograms/mL) that were nontoxic to the confluent host cell cultures.
Chen
X
X
Department of Chemistry, University of South Florida, Tampa 33620-5250.
Schneller
S W
SW
Ikeda
S
S
Snoeck
R
R
Andrei
G
G
Balzarini
J
J
De Clercq
E
E
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D004285:Dogs; D004622:Embryo, Mammalian; D006367:HeLa Cells; D006801:Humans; D009980:Influenza A virus / Q000187:drug effects; D007668:Kidney; D018113:Respiratory Syncytial Virus, Human / Q000187:drug effects; D014616:Vaccinia virus / Q000187:drug effects; D014721:Vesicular stomatitis Indiana virus / Q000187:drug effects; D014780:Viruses / Q000187:drug effects*
D000998:Antiviral Agents; D003853:Deoxyribonucleosides; C084479:5'-deoxypyrazofurin