title: Synthesis, spectroscopy, X-ray crystallography, DFT calculations, DNA binding and molecular docking of a propargyl arms containing Schiff base.
abstract: A propargyl arms containing Schiff base (L) was synthesized by the condensation of 1-[2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethanone with trans-1,2-diaminocyclohexane. The structure of L was characterized by IR, (1)H NMR, (13)C NMR and UV-Vis spectroscopy and by single crystal X-ray diffraction analysis. The UV-Visible spectral behavior of L in different solvents exhibits positive solvatochromism. Density functional calculation of the L in gas phase was performed by using DFT (B3LYP) method with 6-31G basis set. The computed vibrational frequencies and NMR signals of L were compared with the experimental data. Tautomeric stability study inferred that the enolimine is more stable than the ketoamine form. The charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Electronic absorption and emission spectral studies were used to study the binding of L with CT-DNA. The molecular docking was done to identify the interaction of L with A-DNA and B-DNA.
authors.affiliation: Chemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, Thoothukudi District, Tamil Nadu, India.
authors.forename: C
authors.initials: C
authors.lastname: Balakrishnan
authors.affiliation: Chemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, Thoothukudi District, Tamil Nadu, India.
authors.forename: L
authors.initials: L
authors.lastname: Subha
authors.affiliation: Chemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, Thoothukudi District, Tamil Nadu, India. Electronic address: drmaneelakantan@gmail.com.
authors.forename: M A
authors.initials: MA
authors.lastname: Neelakantan
authors.affiliation: Chemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, Thoothukudi District, Tamil Nadu, India.
authors.forename: S S
authors.initials: SS
authors.lastname: Mariappan
mesh_terms: D000480:Alkynes / Q000737:chemistry* / Q000493:pharmacokinetics*; D018360:Crystallography, X-Ray; D003514:Cyclohexylamines / Q000737:chemistry; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D011789:Quantum Theory; D012545:Schiff Bases / Q000737:chemistry* / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D014732:Vibration; D014961:X-Ray Diffraction
chemical_list: D000480:Alkynes; D003514:Cyclohexylamines; D012545:Schiff Bases; D004247:DNA; C030435:1,2-cyclohexanediamine
keywords: DFT calculation; DNA binding; Electronic absorption spectra; Molecular docking; Single crystal analysis