Syntheses and Antitumor Activities of D-and L-2′-Deoxy-4′-thio Pyrimidine Nucleosides

Abstract

Both enantiomers of 2′-deoxy-4′-thiouridine (9) and 15, 4′-thiothymidine (10) and 16, and 2′-deoxy-4′-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-β-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-α, β3-xylofuranoside (1)) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.