Synthesis, structural characterization, DNA binding and antioxidant potency of new ferrocene incorporated acyl ureas

Article abstract of DOI:10.1016/j.jorganchem.2015.08.010

In this article, we have reported the synthesis of three new ferrocene incorporated ureas namely; 1-(4-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea (P4Cl), 1-(3-Chlorobenzoyl)-3-(4-ferrocenyl phenyl)urea (P3Cl) and 1-(2-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea (P2Cl). All new compounds were unambiguously characterized by common analytical techniques (NMR, FT-IR, AAS, CHNS and molecular docking). Furthermore, single crystal XRD analysis was done for 1-(3-Chlorobenzoyl)-3-(4-ferrocenylphenyl)urea. DNA binding is a pre-requisite for a compound to be used as an antitumor agent. The DNA binding study was done by cyclic voltammetry, UV-vis spectroscopy and viscometry. The drug-DNA binding constant was found to vary in the sequence: K_P2Cl (6.056 × 10⁴ M^-1) > K_P4Cl (5.713 × 10⁴ M^-1) > K_P3Cl (4.631 × 10⁴ M^-1). Diffusion coefficient of the drug-DNA adduct for all the compounds is lower than the free drug, indicating that drug-DNA adduct is of higher molecular weight and slow diffusing as compared to the free drug. Small binding site size of 0.440 (P3Cl), 0.585 (P4Cl) and 0.673 (P2Cl) base pairs is consistent with electrostatic interaction. All the compounds exhibited good antioxidant activities with IC₅₀ values of 82, 136 and 54 μM for P4Cl, P3Cl and P2Cl respectively, against DPPH.