Synthesis and bioelectrochemical behavior of aromatic amines

Bioorg Chem. 2017 Dec:75:224-234. doi: 10.1016/j.bioorg.2017.10.002. Epub 2017 Oct 4.

Abstract

Four aromatic amines 1-amino-4-phenoxybenzene (A1), 4-(4-aminophenyloxy) biphenyl (A2), 1-(4-aminophenoxy) naphthalene (A3) and 2-(4-aminophenoxy) naphthalene (A4) were synthesized and characterized by elemental, spectroscopic (FTIR, NMR), mass spectrometric and single crystal X-ray diffraction methods. The compounds crystallized in monoclinic crystal system with space group P21. Intermolecular hydrogen bonds were observed between the amine group and amine/ether acceptors of neighboring molecules. Electrochemical investigations were done using cyclic voltammetry (CV), square wave voltammetry (SWV) and differential pulse voltammetry (DPV). CV studies showed that oxidation of aromatic amines takes place at about 0.9 V (vs. Ag/AgCl) and the electron transfer (ET) process has irreversible nature. After first scan reactive intermediate were generated electrochemically and some other cathodic and anodic peaks also appeared in the succeeding scans. DPV study revealed that ET process is accompanied by one electron. DNA binding study of aromatic amines was performed by CV and UV-visible spectroscopy. These investigations revealed groove binding mode of interaction of aromatic amines with DNA.

Keywords: Aromatics amines; Crystal structures; Drug-DNA interaction study; Electrochemistry.

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Benzene Derivatives / chemistry*
  • Crystallography, X-Ray
  • DNA / chemistry
  • DNA / metabolism
  • Electrochemical Techniques*
  • Electron Transport
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Amines
  • Benzene Derivatives
  • DNA