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Bioorg Med Chem ; 11(3): 357-66, 2003 Feb 06.
Article in English | MEDLINE | ID: mdl-12517431

ABSTRACT

Novel nucleoside analogues of both D and L enantiomeric series were prepared by coupling reaction between a 2',3'-dideoxy-3'-modified furanose moiety and four different nucleobases. Though in all cases anomeric mixtures of nucleosides were obtained, the presence of the sterically bulky 3'-tris(methylthio)methyl group allowed a good stereoselectivity level. All the compounds of both enantiomeric series showed high IC(50) values as HSV-1 TK inhibitors and scarce ability to be phosphorylated by HSV-1 TK. In order to overcome possible problems related to the first phosphorylation step and to facilitate the penetration of the molecule through the cellular membrane, a monophosphate prodrug containing a long lipophilic chain was synthesized. No appreciable antiviral activity was exhibited by this molecule.


Subject(s)
Furans/chemistry , Nucleosides/chemistry , Nucleosides/pharmacology , 3T3 Cells , Animals , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Furans/chemical synthesis , Herpesvirus 1, Human/enzymology , Inhibitory Concentration 50 , Mice , Nucleosides/chemical synthesis , Phosphorylation , Stereoisomerism , Structure-Activity Relationship , Thymidine Kinase/antagonists & inhibitors , Tumor Cells, Cultured
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