Synthesis, spectroscopic characterization (FT-IR, FT-Raman, and NMR), quantum chemical studies and molecular docking of 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione

Spectrochim Acta A Mol Biomol Spectrosc. 2018 Apr 15:195:31-40. doi: 10.1016/j.saa.2018.01.023. Epub 2018 Jan 10.

Abstract

The experimental and theoretical investigations of structure of the 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione were performed. X-ray structure analysis and spectroscopic methods (FTIR and FT-Raman, 1H and 13C NMR), along with the density functional theory calculations (B3LYP functional with empirical dispersion corrections D3BJ in combination with the 6-311 + G(d,p) basis set), were used in order to characterize the molecular structure and spectroscopic behavior of the investigated coumarin derivative. Molecular docking analysis was carried out to identify the potency of inhibition of the title molecule against human's Ubiquinol-Cytochrome C Reductase Binding Protein (UQCRB) and Methylenetetrahydrofolate reductase (MTHFR). The inhibition activity was obtained for ten conformations of ligand inside the proteins.

Keywords: Coumarin; Electrostatic potential; FTIR; Molecular docking; NBO; NMR.

MeSH terms

  • Carrier Proteins / antagonists & inhibitors
  • Chromans / chemistry*
  • Chromans / pharmacology*
  • Humans
  • Magnetic Resonance Spectroscopy / methods*
  • Methylenetetrahydrofolate Reductase (NADPH2) / antagonists & inhibitors
  • Models, Molecular
  • Molecular Conformation
  • Molecular Docking Simulation*
  • Molecular Structure
  • Quantum Theory*
  • Spectroscopy, Fourier Transform Infrared / methods*
  • Spectrum Analysis, Raman / methods*
  • Thermodynamics

Substances

  • Carrier Proteins
  • Chromans
  • ubiquinone-binding proteins
  • MTHFR protein, human
  • Methylenetetrahydrofolate Reductase (NADPH2)