Uracil Derivatives. V. Syntheses and Growth-Inhibitory Activity against L-1210 Cells of 5-Substituted 2'-Deoxyuridines and Orotidine Derivatives

抄録

5-Benzyloxymethyl-2'-deoxyuridine 3', 5'-di-p-toluate (III), a key intermediate in the preparation of 5-substituted 2'-deoxyuridines (VIa-d), was prepared in satisfactory yield. 5-(4-Substituted phenylthiomethyl)-2'-deoxyuridines (VIa-d) were synthesized in three steps from III. The reaction of silylated orotates (VIIa-e) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VIII) gave the N₁, N₃-bisribosides (IXa-e) and the N₃-ribosides (Xa-e). The N₃-ribosides (Xa-e) were deprotected to give the N₃-nucleosides (XIa-e). Compounds VIa-d and XIa-e were tested for ability to inhibit the growth of L-1210 cells in vitro.