Synthesis of 9-[1-(substituted)-3-(phosphonomethoxy)propyl]adenine derivatives as possible antiviral agents.
Acyclic N9 adenine nucleosides substituted at C-1' position were prepared by the Mitsunobu reaction of 1-tert-butyldimethylsilyl-4-pivaloylbutan-1,2,4-triol (5) with adenine. Pivaloyl hydroxyl was modified to the phosphonomethoxy derivatives, and the tert-butyldimethylsilyl hydroxyl was converted to methoxy, azido, amino, fluoro, and c-hydroxyethyl and was eliminated to give vinyl. The resulting phosphonic acids were converted to prodrugs also.
Wu
Minwan
M
BioCryst Pharmaceuticals inc., Birmingham, Alabama 35244, USA.
El-Kattan
Yahya
Y
Lin
Tsu-Hsing
TH
Ghosh
Ajit
A
Vadlakonda
Satish
S
Kotian
Pravin L
PL
Babu
Yarlagadda S
YS
Chand
Pooran
P
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D016174:Hepacivirus / Q000187:drug effects / Q000254:growth & development*; D006801:Humans; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000494:pharmacology; D011355:Prodrugs / Q000138:chemical synthesis* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects*
D000998:Antiviral Agents; D063065:Organophosphonates; D011355:Prodrugs; D000225:Adenine