title: 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.
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 ((1)H, (13)C) 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) 1.4×10(4) and 1.2×10(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.
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. Electronic address: mkhawarrauf@yahoo.co.uk.
authors.forename: Muhammad Khawar
authors.initials: MK
authors.lastname: Rauf
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan; Department of Chemistry, Gomal University, Dera Ismail Khan, Pakistan.
authors.forename: Rukhsana
authors.initials: R
authors.lastname: Gul
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.
authors.forename: Zahid
authors.initials: Z
authors.lastname: Rashid
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. Electronic address: aminbadshah@yahoo.com.
authors.forename: Amin
authors.initials: A
authors.lastname: Badshah
authors.affiliation: Department of Physics, University of Sargodha, Sargodha, Pakistan.
authors.forename: Muhammad Nawaz
authors.initials: MN
authors.lastname: Tahir
authors.affiliation: Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Shahid
authors.affiliation: Department of Chemistry, Gomal University, Dera Ismail Khan, Pakistan.
authors.forename: Azim
authors.initials: A
authors.lastname: Khan
mesh_terms: D000890:Anti-Infective Agents / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D055664:Electrochemical Techniques; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006860:Hydrogen Bonding; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000890:Anti-Infective Agents; D000935:Antifungal Agents; D005296:Ferrous Compounds; D006146:Guanidines; C000600059:N-isopropyl-N-(4-ferrocenylphenyl)-N'-(2,6-diethylphenyl)-N'-benzoylguanidine; D004247:DNA
keywords: Antimicrobial; DFT; DNA binding; Single crystal XRD; Tetra-substituted guanidine