131244-68-3Relevant academic research and scientific papers
Synthesis of 1-(Hydroxyalkoxy)pyrimidines, a Novel Series of Acyclic Nucleoside Analogues
Harnden, Michael R.,Jennings, L. John,Parkin, Ann
, p. 2175 - 2183 (2007/10/02)
Syntheses of 1-(3-hydroxypropoxy), 1-, 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.
