Synthesis and biological evaluation of unsaturated keto and exomethylene d-arabinopyranonucleoside analogs: Novel 5-fluorouracil analogs that target thymidylate synthase KU Leuven
The synthesis of pyrimidine unsaturated keto and exomethylene arabinopyranonucleoside analogs as potential antitumor and antiviral agents is described. Commercially available 1,2,3,4-tetra-O-acetyl-d-arabinopyranose (1) was condensed with silylated thymine, uracil, 5-fluorouracil, N(4)-benzoyl cytosine and 5-(trifluoromethyl)uracil, respectively, deacetylated and acetylated to afford 1-(3,4-O-isopropylidene-α-d-arabinopyranosyl)pyrimidine ...