Synthesis of Tetrazole Oxathiolane Nucleoside Analogues and Their Evaluation as HIV-1 Antiviral Agents |
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Authors: | Philippe Faury Michel Camplo Anne-Sophie Charvet Jean-Claude Chermann Jean-Louis Kraus |
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Affiliation: | 1. Laboratoire de Chimie Biomoléculaire , Faculté des Sciences de Luminy Case , 901, 163 Avenue de Luminy, 13288, Marseille Cedex 9, FRANCE;2. Unité de Recherche INSERM sur les Retrovirus et Maladies Associées U 322 , Campus Universitaire de Luminy , BP 33, 13273, Marseille Cedex 9, France |
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Abstract: | Abstract The synthesis of The synthesis of 2-hydroxymethyl-5-[N2-(5′-carboxamido tetrazolyl)]-1,3-oxathiolane (6a and 6b) and 2-hydroxymethyl-5-[N2-(5′-aminotetrazolyl)]-1,3-oxathiolane (7a and 7b) is described. It involved the preparation of suitable 1,3-oxathiolane precursors via cyclocondensation between benzoyloxyacetaldehyde and 2-mercaptoacetaldehyde di-[2-methoxyethyl] acetal, followed by condensation of adequately substituted tetrazoles using trimethylsilyltriflate or titanium tetrachloride as acid catalysts. In a preliminary in vitro study these new tetrazole oxathiolane nucleoside analogues were found inactive against HIV-1 retrovirus. |
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