Synthesis, structural characterization and anticarcinogenic activity of a new Gly-Gly dipeptide derivative: Methyl 2-(2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate

A new anticarcinogenic Gly-Gly dipeptide derivative, methyl 2-(2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido) acetate, has been synthesized and identified by means of elemental analysis, IR, 1H NMR, 13C NMR, DSC-TGA and X-ray diffraction. It crystallizes in space group P−1 with a = 4.873(4), b = 9.118(7), c = 12.564(10) Å, α = 97.048(15)°, β = 96.159(16)°, γ = 104.987(15)°, Z = 2, V = 533.6(7) Å3, C9H10FN3O5, Mr = 259.2, Dc = 1.613 g/cm3, μ = 0.143 mm−1, F(0 0 0) = 268, R = 0.0626 and wR = 0.1284. In solid state, two adjacent molecules of the title compound are tied to form analogous antiparallel β-sheet arrangement typical of the Gly-Gly dipeptide sequence. The biological test shows that the title compound has certain anticarcinogenic activity, and the cyclic voltammetry test shows the title compound interacts with DNA more strongly than 5-fluorouracil does.