39541-85-0Relevant academic research and scientific papers
Some Chemical Reactions of 5-Vinyluracil and 2'-Deoxy-5-vinyluridine
Jones, A. Stanley,Slater, Martin J.,Walker, Richard T.
, p. 1325 - 1330 (2007/10/02)
In an attempt to elucidate the chemical reactions responsible for the antiviral and toxic properties of 2'-deoxy-5-vinyluridine (1), the chemistry of some 5-vinyluracil derivatives has been studied.Under aqueous acidic conditions 5-vinyluracil (5) is in equilibrium with 5-(1-hydroxyethyl)uracil (6) and the dimer, (E)-1,3-bis(uracil-5-yl)but-1-ene (9).The formation of (9) is favoured in concentrated solution.Upon treatment with aqueous acid compound (1) gives 2'-deoxy-5-(1-hydroxyethyl)uridine (4) but no dimerisation occurs. 1-Ethyl-5-vinyluracil (7) has been synthesized and this in hydrochloric acid gives the dimer, (E)-1,3-bis(1-ethyluracil-5-yl)but-1-ene (10).Under similar conditions compound (5) reacts with L-cysteine to give 5-(1-L-cystein-S-ylethyl)uracil (11) and with phenol to give a mixture of substituted phenols.Compound (1) reacts with butan-1-ol in the presence of trifluoroacetic acid to give 5-(1-butoxyethyl)-2'-deoxyuridine (14); under more vigorous conditions 5-(1-butoxyethyl)uracil (13) was formed.In 1M hydrochloric acid at 100 deg C compound (1) reacts with phenol to give a mixture of substituted phenols.From this mixture 2'-deoxy-5-uridine (17) was isolated and characterised.In a similar manner compound (1) reacted with 4-propan-2-ylphenol to give 2'-deoxy-5-uridine (18).Treatment of compound (1) with m-chloroperbenzoic acid in water-tetrahydrofuran gave 2'-deoxy-5-(1,2-dihydroxyethyl)uridine (19) which was characterised as its tetra-O-acetate (20).
