Synthesis and antiviral activity of 2'-fluorohexopyranosyl nucleosides.
2'-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-position of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.
Jeong
L S
LS
College of Pharmacy, Ewha Womans University, Seoul, Korea.
Lee
J E
JE
Kim
H O
HO
Chun
M W
MW
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy
D000998:Antiviral Agents; D000241:Adenosine