Synthesis, chemical characterization, DNA interaction and antioxidant studies of ortho, meta and para fluoro substituted ferrocene incorporated selenoureas

Abstract

We have reported a one pot synthesis of three new ferrocene incorporated selenoureas namely; 1-(2-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP2F), 1-(3-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP3F) and 1-(4-fluorobenzoyl)-3-(4-ferrocenyl-3-methylphenyl)selenourea (MeP2F) by the reaction of corresponding carboxylic acid chlorides with potassium selenocyanate (KSeCN) and 3-methyl-4-ferrocenyl aniline in acetone under constant stirring. Synthesized compounds were characterized by FTIR, NMR (1H and 13C), CHNS and AAS. We have also presented X-rays single crystal structure for MeP2F. DNA binding studies were evaluated with the help of cyclic voltammetry in the presence of TBAP (tertiary butyl ammonium perchlorate) as supporting electrolyte in DMSO/water mixture of 70:30. Binding constant for MeP2F is 1.499 ×103M−1, MeP3F is 1.706 ×103M−1 and MeP4F is 1.035×103M−1. Binding site size for MeP2F (0.334bp)<MeP4F (0.410bp)<MeP3F (0.463bp). In all the compounds diffusion coefficients of drug-DNA adduct is lower than the free drug indicating slow diffusion of comparatively high molecular weight drug towards the electrode in cyclic voltammetry. Mode of interaction has further been reconfirmed with the help of viscometry. All the three compounds have good antioxidant activities against DPPH with IC50 values of 132, 108 and 84μg/ml for MeP2F, MeP4F and MeP3F respectively.