A Novel Type of Spironucleosides: 2′,5′-O-bis-TBDMS Uridine-3′-spiro-3′-isoxazolidin-5′-one and Its Thymidine Congener |
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| Authors: | Jean M J Tronchet Imre Kovacs Françoise Barbalat-Rey Naz Dolatshahi |
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| Institution: | Department of Pharmaceutical Chemistry , Faculty of Sciences , 30 Quai Ernest Ansermet, 1211 , Geneva , 4, Switzerland |
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| Abstract: | Abstract TSAO analogues, 2′,5′-O-bis-TBDMS uridine-3′-spiro-3′-isoxazolidin-5′-one (9) and its thymidine congener 10, as well as model spiro sugar derivatives (3 and 4) have been prepared from the corresponding nitrones through a stereospecific tandem nucleophilic attack. Compounds 9 and 10 which are bioisosters of TSAO-U and T respectively but which lack an amino group on the spiro ring, were found inactive against both HIV-1 and HIV-2. |
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