Synthesis and biological evaluation of isonucleosides derived from methyl 3,5-anhydro-2-O-(2-fluorobenzyl)-D-xylofuranosides.
New isonucleosides [methyl 5-(1-pyrimidinyl)furanosides] are prepared by nucleophilic opening of the oxetane ring of methyl 3,5-anhydro-2-O-(2-fluorobenzyl)-D-xylofuranoside with silylated pyrimidine bases in the presence of trimethylsilyl triflate. Structures, configurations and conformations were determined by NMR techniques and several X-ray diffraction analyses, seven of the isonucleosides were tested for cytotoxicity and activity against HIV, HSV and several other viruses.
Wirsching
Jörn
J
Institut für Organische Chemie der Universität Hamburg, Germany.
Schulze
Oliver
O
Voss
Jürgen
J
Giesler
Anja
A
Kopf
Jürgen
J
Adiwidjaja
Gunadi
G
Balzarini
Jan
J
De Clercq
Erik
E
D000818:Animals; D019380:Anti-HIV Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D005663:Furans; D009705:Nucleosides