Journal of the Chemical Society. Perkin transactions I p. 2175 - 2183 (1990)
Update date:2022-08-05
Topics:
Harnden, Michael R.
Jennings, L. John
Parkin, Ann
Syntheses of 1-(3-hydroxypropoxy), 1-<3-hydroxy-2-(hydroxymethyl)propoxy>, 1-(2,3-dihydroxypropoxy), and 1-(3,4-dihydroxybutoxy) derivatives of thymine (1a-d) and uracil (2a-d) are described.These acyclonucleosides were obtained by cyclisation of appropriately functionalised ureas with either ethyl 3,3-diethoxy-2-methylpropionate (4) or methyl 3,3-dimethoxypropionate (5).The uracils (2a-d) were converted into cytosine analogues (3a-d) via intermediate 4-(1,2,4-triazol-1-yl) derivatives. (E)-5-(2-Bromovinyl) (36) and 5-vinyl (37) analogues of (2a) were prepared by palladium(II)-catalysed cross-coupling reactions on the 5-iododerivative (32).The 5-fluoro-1-(hydroxyalkoxy)uracils (41) and (42) were obtained by alkylation of 5-fluoro-1-hydroxyuracil with a suitably functionalised halide.None of this series of acyclonucleosides showed activity in antiviral tests in cell cultures.
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