A series of amino acid ester derivatives containing 5-fluorouracil were synthesized using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N-hydroxybenzotriazole (HOBt) as a coupling agent. The structures of the products were assigned by NMR, MS, IR etc. The in vitro antitumor activity tests against leukaemia HL-60 and liver cancer BEL-7402 indicated that (R)-ethyl 2-(2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(4-hydroxyphenyl) propanoate showed more inhibitory effect against BEL-7402 than 5-FU.
The title compound, C11H9NO5, was prepared by the reaction of 2-furanacrylic acid and N-hydroxysuccinimide. The molecule consists of two approximately planar moieties, viz. a succinimide group and the rest of the molecule [the largest deviations from the least-squares planes are 0.120 (1) and 0.210 (1) Å, respectively]. The dihedral angle between these fragments is 63.70 (5)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into two-dimensional nets.
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