Thiosugars. Part 5: synthesis and biological activity of 1-(4-thio-L-arabinofuranosyl)-5-halopyrimidine nucleosides.
1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabinofuranoside (6) was transformed in two steps into the 1-(4-thio-L-arabinofuranosyl)-5-halopyrimidine nucleosides 10, 11 and 12, obtained as anomeric mixtures which were separable in the case of 10 and 11. No in vitro antiviral activity against HIV-1 and HIV-2. TK+ and TK- VZV and CMV has been found for 10, 11 and 12.
Wirsching
J
J
Institut für Organische Chemie der Universität Hamburg, Germany.
Voss
J
J
Balzarini
J
J
De Clercq
E
E
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D003587:Cytomegalovirus / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D014645:Herpesvirus 3, Human / Q000187:drug effects; D009005:Monosaccharides / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D011743:Pyrimidines / Q000737:chemistry*
C415645:1-(4-thio-arabinofuranosyl)-5-halopyrimidine; D000998:Antiviral Agents; D009005:Monosaccharides; D009705:Nucleosides; D011743:Pyrimidines