Quinazolinone is a an important heterocyclic compound possessing a wide range of biological activities such as anti-tumour, sedative, antidiabetic, analgesic, anti-inflammatory, antimicrobial and anticancer. It is a versatile lead molecule for the design of potential bioactive agents. They show anti-inflammatory and analgesic action by inhibiting the microsomal prostaglandin E2-synthase 1 (mPGES-1) which is a key enzyme of the arachidonic acid. The aim of the present study includes the synthesis of some novel Schiff bases of amino derivatives of quinazolinone as anti-inflammatory and analgesic agent. A new series of the title compounds incorporated into diverse N heterocyclic moieties. First step involves the synthesis of 6,8-diiodo-2-phenyl-4H-3,1- benzoxazin-4-one. In second step this compound reacts with hydrazine hydrate to form a new intermediate 6,8-diiodo-2-phenylquinazolin-4(3H)-one. Schiff bases (5a-5f) were synthesized by the reaction of 6,8-diiodo-2-phenylquinazolin-4(3H)-one with different aromatic aldehydes. Maximum yield of 79% was obtained from p-hydroxy derivative. Schiff bases formed were evaluated for anti-inflammatory and analgesic activities. O-hydroxy derivative showed maximum anti-inflammatory activity with percentage inhibition of 50.45%. It was proved to be good analgesic agent as well. It was concluded that Schiff bases containing hydroxyl group showed promising activity as compared to chloro derivatives.