Abstract: A series of new 5-(4-chlorophenyl)-9-iodo-3-substituted-1,2,4-triazolo[4,3-c]quinazoline and 2- (4-chlorophenyl)-6-iodo-4-substituted-quinazoline was prepared via several synthetic routes. Some of the compounds were prepared by cyclization of 2-(4-chlorophenyl)-4-chloro-6-iodoquinazoline with semicarbazide or acid hydrazide; other compounds were obtained from reaction of 2-(4-chlorophenyl)-4-chloro-6-iodoquinazoline with some amines and amino acid esters. The synthesized compounds were evaluated as anti-inflammatory agents through the carrageenin-induced paw edema test. The screening data revealed that nine of the tested compounds have activity comparable to indomethacin.