Design and synthesis of vidarabine prodrugs as antiviral agents.
5'-O-D- and L-amino acid derivatives and 5'-O-(D- and L-amino acid methyl ester phosphoramidate) derivatives of vidarabine (ara-A) were synthesized as vidarabine prodrugs. Some compounds were equi- or more potent in vitro than vidarabine against two pox viruses and their uptake by cultured cells was improved compared to the parent drug.
Shen
Wei
W
TSRL Inc., 540 Avis Drive Suite A, Ann Arbor, MI 48108, USA. wshen@tsrlinc.com
Kim
Jae-Seung
JS
Kish
Phillip E
PE
Zhang
Jie
J
Mitchell
Stefanie
S
Gentry
Brian G
BG
Breitenbach
Julie M
JM
Drach
John C
JC
Hilfinger
John
J
D000284:Administration, Oral; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001087:Arabinonucleosides / Q000737:chemistry; D018938:Caco-2 Cells; D002478:Cells, Cultured; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004952:Esters; D006367:HeLa Cells; D006801:Humans; D007982:Levulinic Acids / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry; D011212:Poxviridae / Q000378:metabolism; D011355:Prodrugs / Q000138:chemical synthesis* / Q000494:pharmacology; D014740:Vidarabine / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D001087:Arabinonucleosides; D004952:Esters; D007982:Levulinic Acids; D009705:Nucleosides; D011355:Prodrugs; C008099:hypoxanthine arabinoside; D014740:Vidarabine; C032246:levulinic acid