3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine.
3',3'-Difluoro-3'-deoxythymidine (3) has been synthesized in four steps from thymidine, and characterized by 1H NMR and NOE experiments. The JHF coupling constants support a conformation in solution that is predominantly 2'-endo (S). Although conformationally and sterically nucleoside 3 may resemble other thymidine analogs which are active against HIV-1, 3 is virtually inactive.
Bergstrom
D E
DE
Department of Medicinal Chemistry and Pharmacognosy, Purdue University, West Lafayette, Indiana 47907.
Mott
A W
AW
De Clercq
E
E
Balzarini
J
J
Swartling
D J
DJ
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D015224:Dideoxynucleosides / Q000138:chemical synthesis / Q000494:pharmacology*; D006678:HIV / Q000187:drug effects*; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D015224:Dideoxynucleosides; C076821:3',3'-difluoro-3'-deoxythymidine; C002854:alovudine