Synthesis, docking and biological activity of antimetabolites based on uraciles and 5-substituted 2,6-dimethylpyrimidin-4(3<i>h</i>)-ones

Abstract

5-Substituted 2,4-dimethyl-1,6-dihydropyrimidin-6-ones reacted with aromatic aldehydes to form 5-substituted (Z)-2-(2-aryl)-1-ethenylpyrimidin-6-ones, and in the reaction of 5-(4-fluorobenzyl)-2,6-dimethylpyrimidin-4(3 H )-one with 4-fluorobenzaldehyde, 5-(4-fluorobenzyl)-2,6-bis[( E )-4-fluorostyryl]pyrimidin-4(3 H )-one. Uracil and 5-fluorouracil were alkylated with 4-methoxy-2-chloromethylbenzaldehyde to give 2-[2,4-dioxoand 5-fluoro-2,4-dioxo-3,4-dihydropyrimidine-1(2 H )methyl]-4-methoxybenzaldehydes and are condensed with 5-substituted 2,4-dimethyl-1,6-dihydropyrimidin-6-ones to form 1-{5[( E )-2-(5-butyl-, arylmethyl-4-methyl6-oxo-1,6-dihydro-pyrimidin-2-yl)vinyl]-2-methoxybenzyl}uracil, 5-fluorouracil, and 5-bromouracil. The results of docking studies and data on the antibacterial, antitumor, and antimonoamine oxidase activity of the synthesized compounds are presented.