[Synthesis and bioaction of 2-alkyl-4(1H)-quinolone]

Five quinolone alkaloids (IVa, Va, c, d, g) including two new compounds (IVa, Vc) from Evodia rutaecarpa and nine analogs are synthesized in good yield by using acid-catalyzed condensation of a series of 3-oxoalkkanoic acid esters with aniline and further methylized with methyl iodide. The other analogue Vh is prepared through the reaction of lithium enolate methyl ketone with N-methylisatoic anhydride. Eight compounds (IVa, d, f; Vb, c, d, f, h) were synthesized for the first time. Pharmacological studies showed that these compounds have vasoconstriction inhibiting and antiulcer effects. Compound IVb also has cytotoxic effect.