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Synthesis of quinazolindionyl amino acid and dipeptide derivatives as possible antitumour agents

Some physiologically active amino acid and dipeptide esters were coupled to 3-(2-hydroxyethyl)-2,4-dioxo(1H,3H)-quinazoline at N-1 via acetyl/propionyl link. The C2/C3 anchor segments were introduced by either alkylation or Michael addition reactions with ethyl chloroacetate or methyl acrylate respectively. The occurrence of these two reactions on nitrogen N-1 rather than oxygen atom was confirmed by spectral values (1H and 13C NMR). Amide bond formation was performed by the azide activation procedure at 0 oC to avoid Curtius rearrangement. 21 of the newly synthesized compounds exhibited IC50’s in the range of 5.63-26.9 μg/mL relative to doxorubicin (3.23 μg/mL) when tested against HepG2cell line.