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Ten new C3, 6-dibenzoylated thiosemicarbazone-chitosan derivatives (with two different molecular weights) were prepared. The purpose of this study was to further investigate the antioxidant activities of this series of derivatives and the relationship between the structure and their antioxidant behavior. In order to know how the structure influenced the antioxidant activities of the derivatives, their structures were characterized by FT-IR spectroscopy and elemental analysis in this paper. In addition, the antioxidant activities of these new derivatives were also researched employing various established systems, such as hydroxyl radical (•OH)/superoxide anion (O2 −)/DPPH scavenging and reducing power. Besides that, the cell toxicity of those derivatives was determined with MTT method. The results indicated that 3,6-DBZPTSCZLCS, 3,6-DBZ(p-NP)TSCZLCS, 3,6-DBZ(o-CP)TSCZHCS, and 3,6-DBZ(p-NP)TSCZHCS had the potential to be used as natural antioxidants because of their excellent activities in all these assays. O O O O NH2 C S NNH C NH C NNH C S NH 3,6-DBZPTSCZCS 3,6-DBZPTSCZHCS , Mw= 200 KDa ; 3,6-DBZPTSCZLCS , Mw= 3 KDa . n Ten new 3, 6-diacetylated phenyl-thiosemicarbazone-chitosans were synthesized and characterized. The antioxidant activities of the derivatives were investigated.