Synthesis, Crystal Structure, Spectral And Electrochemical Characterization, DNA Binding and Antioxidant studies of 1-(2- florobenzoyl)-3-(2-chloro, 4-ferrocenylphenyl) thiourea

Abstract

In this manuscript we have synthesized systematically 1-(2-florobenzoyl)-3-(2-chloro, 4-ferrocenylphenyl) thiourea (2F) and successfully determined the structure by single crystal X-rays diffraction analysis. The compound was spectrally characterized using multinuclear 1H and 13C nuclear magnetic resonance (NMR) and fourier transform infra-red (FT-IR) spectroscopic techniques and electrochemical characterization was carried out using cyclic voltammetry. The compound (2F) was then screened for potential deoxyribonucleic acid (DNA) binding and antioxidant activity. The single crystal XRD title compound 2F showed that ferrocenyl moiety had eclipsed conformation while the phenyl ring substituted on ferrocenyl is not in plane with cp-ring. The compound (2F) had shown a reversible process with one electron transfer, two peaks were observed for oxidation and reduction during scan. From voltametric measurements, the shifts in peak potential and peak current were used to review the mode of interaction which is found to be noncovalent electrostatic, drug-DNA binding constant and diffusion coefficients of the compound (2F) and 2F-DNA adduct. The binding constant (M-1) was found to be 2.92 × 103 with binding energy 19.76 kJ mol-1. The diffusion coefficient of free compound (2F) was calculated 1.75 × 10-7 whereas diffusion coefficient of 2F-DNA was found to less to i.e. 8.96 × 10-8 which was obvious as free molecules are easy to diffuse because of its low molecular weight whereas 2F interacted with DNA become heavier and the quantity of remained free molecules became less as a result decrease in current was observed. The compound (2F) showed significant activity with IC50 value 41.69 μg mL-1 using 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay.