Synthesis of 9-[1-(1 -hydroxyethyl)-3-(phosphonomethoxy)propyl]adenine and prodrug as possible antiviral agents.
The appropriately protected C-1'-hydroxyethyl-3-hydroxypropyl-N9-adenine nucleoside was prepared from 1-pivaloyloxy-5-tert-butyldiphenylsilyloxy-3-pentanol and adenine through the Mitsunobu reaction. One of the terminal hydroxyls was converted to the phosphonomethoxy derivative and the prodrug.
Ghosh
Ajit
A
BioCryst Pharmaceuticals Inc., Birmingham, AL 35244, USA.
El-Kattan
Yahya
Y
Wu
Minwan
M
Lin
Tsu-Hsing
TH
Vadlakonda
Satish
S
Kotian
Pravin L
PL
Babu
Yarlagadda S
YS
Chand
Pooran
P
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D016174:Hepacivirus / Q000187:drug effects / Q000254:growth & development*; 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