3',3'-Difluoro-3'-deoxythymidine: comparison of anti-HIV activity to 3'-fluoro-3'-deoxythymidine

J Med Chem. 1992 Sep 4;35(18):3369-72. doi: 10.1021/jm00096a011.


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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology*
  • Dideoxynucleosides / chemical synthesis
  • Dideoxynucleosides / pharmacology*
  • HIV / drug effects*
  • Molecular Conformation
  • Structure-Activity Relationship


  • Antiviral Agents
  • Dideoxynucleosides
  • 3',3'-difluoro-3'-deoxythymidine
  • alovudine