       Document 0149
 DOCN  M9640149
 TI    Synthesis and anti-HIV-1 activity of novel TSAO-T derivatives modified
       at the 2'- and 5'-positions of the sugar moiety.
 DT    9604
 AU    Ingate S; Perez-Perez MJ; De Clercq E; Balzarini J; Camarasa MJ;
       Instituto de Quimica Medica (C.S.I.C.), Madrid, Spain.
 SO    Antiviral Res. 1995 Jun;27(3):281-99. Unique Identifier : AIDSLINE
       MED/96145337
 AB    Novel analogues of the anti-HIV-1 agent TSAO-T, [1-[2',5'-bis-O-(tert-
       butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5-(4- amino-
       1,2-oxathiole-2,2-dioxide) and its 3-methyl counterpart TSAO-m3T were
       obtained by modifications at positions 2' or 5' of the sugar moiety.
       These compounds were evaluated for their inhibitory effect on HIV-1 and
       HIV-2 replication in cell culture. Introduction of new groups at the
       5'-position (i.e. esters, benzylether and silylethers) resulted in
       compounds that were either inactive or less active than the parent
       compounds (TSAO-T and TSAO-m3T). Attempts to introduce small silyl ether
       groups at this position were not successful since these products
       decomposed during purification. Similar modifications at the 2'-position
       had a much less pronounced influence on the anti-HIV-1 activity.
 DE    Antiviral Agents/CHEMICAL SYNTHESIS/*PHARMACOLOGY
       Carbohydrates/*CHEMISTRY  Cell Line  Human  HIV-1/*DRUG EFFECTS
       HIV-2/*DRUG EFFECTS  Reverse Transcriptase Inhibitors/CHEMICAL
       SYNTHESIS/*PHARMACOLOGY  Spiro Compounds/CHEMICAL
       SYNTHESIS/*PHARMACOLOGY  Structure-Activity Relationship  Support,
       Non-U.S. Gov't  Thymidine/*ANALOGS & DERIVATIVES/CHEMICAL
       SYNTHESIS/PHARMACOLOGY  Virus Replication/DRUG EFFECTS  JOURNAL ARTICLE

       SOURCE: National Library of Medicine.  NOTICE: This material may be
       protected by Copyright Law (Title 17, U.S.Code).

