Macrocyclic peptides are very important in bioorganic and medicinal chemistry investigations. Synthesis and chemical modifications of existing antibacterial agents in order to generate novel macromolecules with better therapeutic properties are necessary. A series of macrocyclic pentapeptide Schiff bases 3-10 were synthesized from the reaction of Nα-dinicotinoyl-bis (L-leucyl-L-phenylalaninyl acid hydrazide) (1) and the macrocyclic pentapeptide ester (2) with selected dibasic amino acid and active reagents. All prepared compounds were tested as anti-inflammatory, analgesic and anticonvulsant agents. Some of the screened compounds exhibited better anti-inflammatory, analgesic and anticonvulsant activities comparable to prednisolone®, valdecoxib and carbamazepine as reference drugs.