Synthesis and antiinflammatory screening of some quinazoline and quinazolyl-4-oxoquinazoline derivatives

Abstract

Synthesis of some new derivatives of 2-aryl-4-oxo-l-(4-quinazolyl)quinazolines is described. Methyl N-(4-quinazolyl)anthranilate was allowed to react with phenyl iso(thio)cyanate to give 3-phenyl-1-(4-quinazolyl)-1,2,3,4-tetrahydro-2,4-dioxo-and 4-oxo-2-thioxoquinazolines (3 a and 3 b, respectively) Alternatively, anthranilic acid amide derivatives were subjected to cyclization with aromatic aldehydes to give 2-aryl-4-oxo-1-(4-quinazolyl)-1,2,3,4-tetrahydroquinazolines 5. On the other hand, 2-chloro-4-(4-substituted 1-piperazinyl)quinazoline derivatives were subjected to the same type of reactions at the 2-position to afford the corresponding quinazoline derivatives 8 and 10, respectively. Furthermore, the acid amide 4b was cyclized with acid chlorides to give the corresponding 2-aryl-l-(2-chloro-4-quinazolyl)-4-oxo-1,4-dihydroquinazolines 11, from which the triazoloquinazoline derivatives 13 and 15 were synthesized through the intermediate hydrazine derivatives 12. Most of the newly synthesized compounds were tested for their antiinflammatory activities. However, some of the novel compounds were found to exhibit good antiinflammatory potencies.