A new series of N-substituted phthalimide derivatives were prepared by condensation of appropriate amount of n-amino tetrachlorophthalimide with respective aldehyde in glacial acetic acid. The structural investigation of the synthesized compounds was done by spectroscopic methods (UV-Vis., IR, 1 H and 13 C NMR) and elemental analysis. The antibacterial screening of these compounds was performed against Escherichia coli and Staphylococcus mutans. The synthesized compounds were evaluated for their antioxidant potential using 2,2-diphenyl-1-picrylhydrazyl (DPPH) as a scavenging agent. The interaction ability of most promising compounds (3a and 3b) with native calf thymus DNA (Ct-DNA) was also studied by means of UV-Vis., circular dichroism (CD), viscosity measurements and thermal studies. The intrinsic binding constants (Kb) of 3a and 3b with Ct-DNA obtained from UV-Vis. absorption studies were 8 × 10 4 and 1 × 10 5 , respectively. Molecular docking of target compounds (3a and 3b) against DNA dodecamer d (CGCGAATTCGCG)2 has been carried out. The test compounds exhibited remarkable antibacterial, antioxidant and DNA binding activities.
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