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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

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
DOI: 10.1016/j.saa.2014.09.134
  • Tetra-Substituted Guanidine
  • Single Crystal Xrd
  • Dna Binding
  • Antimicrobial
  • Dft
  • Chemistry
  • Design
  • Physics


Abstract A novel tetra-substituted guanidine, N-isopropyl-N-(4-ferrocenylphenyl)-N’- (2,6-diethylphenyl)-N’’-benzoylguanidine (1), [(CH3)2CH)(C5H5FeC5H4C6H4)NC(NHCOC6H5)(NHC6H3(CH2CH3)2] has been synthesized and characterized by elemental analysis, FT-IR, multinuclear (1H, 13C) 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...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 104 and 1.2 x 104 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.

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