A new series of 2,3-disubstituted quinazolinones was synthesised via the reaction of readily obtainable 2-thioxo-3-phenylquinazolin-4(3H)-one 1 with ethyl chloroacetate followed by hydrazinolysis to afford the hydrazide 3. This was allowed to react with different electrophilic reagents such as carbon disulfide, phenyl isothiocyanate, β-diketones, anhydrides, acrylonitrile, ethyl cinnamate, aldehydes, arylidene malononitrile and lauroyl chloride. Some of the newly synthesised compounds showed promising anti-inflammatory activities.