DFT, Molecular Docking and Drug-likeness Analysis: Acrylate molecule bearing perfluorinated pendant unit


Soykan U., Sert Y., Yildirim G.

JOURNAL OF MOLECULAR STRUCTURE, vol.1244, 2021 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1244
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.130940
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Keywords: DFT, HOMO-LUMO, MEP, molecular docking, drug-likeness, NMR CHEMICAL-SHIFTS, FT-IR, C-13 NMR, VIBRATIONAL-SPECTRA, SURFACE-PROPERTIES, SIDE-GROUPS, RAMAN, POLYMERS, MEP, SPECTROSCOPY

Abstract

In this study, 2-oxo-1,1-diphenyl-2-((3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) oxy)ethyl acrylate (ODDFA) molecule was synthesized by the condensation reaction method and the detailed characterization of ODDFA was experimentally and theoretically performed for the first time. As for the theoretical work, molecular geometry, vibrational frequencies, chemical shifts (H-1 and C-13), electrochemical properties and the molecular electrostatic potential (MEP) were investigated with density functional theory method (DFT, B3LYP) at the standard 6-311++G(d,p) level of calculation in the ground state. Moreover, molecular docking simulation and drug-likeness studies of title compound are carried out to determine the pharmacy potential for the title molecule. Bond lengths and angles, the electron engagements, conjugative effect, lone pairs of electrons and possible intra-molecular charge transfer regions regarding the most favored molecular structure of the ODDFA are discussed in detail. The obtained results show that mostly all the computations and experimental results are noted to be in a good correlation with each other. HOMOLUMO analysis also depicts that the pi-pi* conjugations are concentrated on the phenyl rings and carbonyl groups as well as ODDFA molecule possesses the kinetic chemical stability. As for the MEP examination, there exist both the nucleophilic and electrophilic reactive regions together over the surface of molecule thanks to the existence of both the polar and apolar functional groups in the molecule. Moreover, the molecular docking studies confirm that the ODDFA compound studied have the strong potential to behave as the potent inhibitor for tyrosinase with the PDE code of 5I38. Drug-likeness analysis also reveals that the molecule possesses considerable molinspiration bioactivity. (C) 2021 Elsevier B.V. All rights reserved.