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) A, α = 97.048(15)°, β = 96.159(16)°, γ = 104.987(15)°, Z = 2, V = 533.6(7) A3, 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.