Vibrational spectroscopic and molecular docking study of (2E)-N-(4-chloro-2-oxo-1,2-dihydroquinolin-3-yl)-3-phenylprop-2-enamide

Spectrochim Acta A Mol Biomol Spectrosc. 2015:151:335-49. doi: 10.1016/j.saa.2015.06.083. Epub 2015 Jun 23.

Abstract

FT-IR and FT-Raman spectra of (2E)-N-(4-chloro-2-oxo-1,2-dihydroquinolin-3-yl)-3-phenylprop-2-enamide were recorded and analyzed experimentally and theoretically. The synthesis, (1)H NMR and PES scan results are also discussed. Nonlinear optical behavior of the examined molecule was investigated by the determination of first hyperpolarizability. The calculated HOMO and LUMO energies show the chemical activity of the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. From the MEP it is evident that the negative charge covers the carbonyl group and the positive region is over the NH group. The calculated geometrical parameters (SDD) are in agreement with that of similar derivatives. Molecular docking simulations against targets from Mycobacterium tuberculosis are reported and the results suggest that the compound might exhibit inhibitory activity against PknB.

Keywords: DFT; FT-IR; FT-Raman; MEP; Molecular docking; Quinoline.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amides / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Models, Molecular
  • Molecular Docking Simulation*
  • Mycobacterium tuberculosis / drug effects
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Quantum Theory*
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Spectrum Analysis, Raman
  • Vibration*

Substances

  • (2E)-N-(4-chloro-2-oxo-1,2-dihydroquinolin-3-yl)-3-phenylprop-2-enamide
  • Amides
  • Anti-Bacterial Agents
  • Quinolines
  • PknB protein, Mycobacterium tuberculosis
  • Protein Serine-Threonine Kinases