SYNTHESIS AND BIOLOGICAL EVALUATION OF ISONUCLEOSIDES DERIVED FROM METHYL 3,5-ANHYDRO-2-O-(2-FLUOROBENZYL)-d-XYLOFURANOSIDES

Abstract

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.

ACKNOWLEDGMENTS

We thank the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie and the European Commission for their financial support. We also thank Mrs. Ann Absillis, Mrs. Anita Camps and Mrs. Lies Vandenheurck for technical assistance. The BAYER AG, Leverkusen, provided valuable chemicals.