Synthesis, characterization, DNA binding and in vitro antimicrobial studies of a novel tetra-substituted N-isopropyl-N-(4-ferrocenylphenyl)-N′-(2,6-diethylphenyl)-N"-benzoylguanidine: Crystallographic structure and quantum chemical computations

A novel tetra-substituted guanidine, N-isopropyl-N-(4-ferrocenylphenyl)-N'-(2,6-diethylphenyl)-N"-benzoylguanidine (1), [(CH3)(2)CH)(C5H5FeC5H4C6H4)NC(NHCOC6H5)(NHC6H3(CH2CH3)(2)] has been synthesized and characterized by elemental analysis, FT-IR, multinuclear (H-1, C-13) NMR spectroscopy, single crystal X-rays diffraction analysis and density functional theory based quantum chemical calculations. The torsion angles indicating that the guanidine moiety and carbonyl group are almost co-planar, due to the pseudo hexagonal ring formed by intramolecular N-H center dot center dot center dot O hydrogen bonds. The DNA interaction studies performed by cyclic voltammetry and UV-visible spectroscopy are in close agreement with the binding constants (K) 1.4 x 10(4) and 1.2 x 10(4) respectively. The shift in peak potential, current and absorption maxima of the studied ferrocenyl guanidine in the presence of DNA discovered that CV coupled with UV-vis spectroscopy could provide an opportunity to elaborate DNA interaction mechanism, a prerequisite for the design of new drug like agents and understanding the molecular basis of their action. The synthesized compound (1) has also been screened for their antibacterial and antifungal. (C) 2014 Elsevier B.V. All rights reserved.