5'-Fluoro-5'-deoxyaristeromycin.
5'-Fluoro-5'-deoxyaristeromycin (2) has been prepared via a Mitsunobu coupling of (1S,2S,3R,4S)-2,3-(cyclopentylidenedioxy)-4-fluoromethylcyclopentan-1-ol with N6-bis-boc protected adenine. This procedure is adaptable to preparing a number of 5'-fluoro-5'-deoxycarbocyclic nucleoside analogs with diversity in the heterocyclic base. Antiviral analysis found promising activity for 2 toward measles but no other viruses. No cytotoxicity was observed for 2.
Li
Weikuan
W
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, USA.
Yin
Xueqiang
X
Schneller
Stewart W
SW
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002460:Cell Line; D002522:Chlorocebus aethiops; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000494:pharmacology; D014709:Vero Cells
C526405:5'-fluoro-5'-deoxyaristeromycin; D000998:Antiviral Agents; D003839:Deoxyadenosines; D006845:Hydrocarbons, Fluorinated; C030034:aristeromycin; D000241:Adenosine