Abstract
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
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Comparative Study
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antiviral Agents / chemical synthesis
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Antiviral Agents / pharmacology*
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Dideoxynucleosides / chemical synthesis
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Dideoxynucleosides / pharmacology*
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HIV / drug effects*
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Molecular Conformation
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Structure-Activity Relationship
Substances
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Antiviral Agents
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Dideoxynucleosides
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3',3'-difluoro-3'-deoxythymidine
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alovudine