New supramolecular ferrocene incorporated N,N′-disubstituted thioureas: synthesis, characterization, DNA binding, and antioxidant studies

Abstract

Ferrocene incorporated N,N′-disubstituted thioureas (S1–S6) were synthesized by allowing 4-ferrocenyl-3-methylaniline to react with freshly prepared aliphatic isothiocyanates and were characterized by using different analytical techniques. Based on single-crystal X-ray analysis compound S1 shows supramolecular structure mediated by secondary bonding interactions, intermolecular hydrogen bonding NH–O, NH–S, and secondary non-covalent interactions (π–H). Voltammetric measurements were used to study their redox behavior and DNA binding of the compounds. Different binding parameters like binding constants, binding energies, and diffusion coefficients (D_o) were calculated for further insight on the affinity with DNA. All the compounds show electrostatic mode of interactions. The D_o of molecule-DNA adducts were found to be lower than that of free molecule. Compounds S1–S6 having 50% inhibition values less than 37.89 μg mL⁻¹ indicate that they may have value as antioxidants to be used as therapeutic agents.

Graphical Abstract

This research article describes the synthesis, structural characterization, electrochemistry, nature and extent of binding with the DNA and free radical scavenging activity of new ferrocene based N, N′-disubstituted thioureas.

Keywords:

• Ferrocene
• Crystal structure
• Electrochemistry
• DNA binding
• Antioxidant activity

Acknowledgements

The authors are grateful to Quaid-i-Azam University and Higher Education Commission (HEC) Islamabad [grant number PD-IPFP/HRD/HEC/2013/30240], Pakistan.