Docking of disordered independent molecules of novel crystal structure of (N-(4-methoxyphenyl)-2-(3-methyl-2-oxo-3,4-dihydroquinoxalin-1(2H)-yl)acetamide as anti-COVID-19 and anti-Alzheimer's disease. Crystal structure, HSA/DFT/XRD

Missioui M., Said M. A., Demirtas G., Mague J. T., Ramli Y.

JOURNAL OF MOLECULAR STRUCTURE, vol.1247, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1247
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2021.131420
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Quinoxaline, Crystal structure, Gap energy, DFT, Hirshfeld surface analysis (HSA), In silico molecular docking, COVID-19, Alzheimer's disease, COVID-19, CHEMISTRY, ANAKINRA, DESIGN, SAFETY, DFT
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

New quinoxaline derivative, N-(4-methyl-2-nitrophenyl)-2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide (NMPOQA= disordered molecules NMPOQAa(50.3% and NMPOQAb(49.7%)) has been synthesized and characterized by ESI-MS, IR, H-1 & C-13 NMR. The geometric parameters of NMPOQA compound which crystallographic structure has been defined by X-ray diffraction have been calculated by Density Functional Theory (DFT), B3LYP, 6-311 ++ G(d,p) basis set. The correlation between experimental and theoretical structure was checked by superimposing the experimental and theoretical structure. Frontier Molecular Orbitals (FMO's) have been created and the gap energy between High Occupied Molecular Orbital (HOMO) and Low Unoccupied Molecular Orbital (LUMO) has been calculated. Additionally, Molecular Electrostatic Potential (MEP) and Hirshfeld studies have been conducted to analyze intermolecular interactions. Interesting molecular docking of NMPOQA and Remdesivir drug with 6M03 was conducted using the same parameters for a fair comparison. A low binding affinity of the NMPOQA (-6.9 kcal/mol) compared to the Remdesivir drug, (-7.1 kcal/mol) and other good reasons make NMPOQA a good candidate against COVID-19. A similar study was calculated with 1EVE producing evidences that suggest NMPOQA may serve as a potential drug for developing Alzheimer's disease (AD) treatment (C) 2021 Elsevier B.V. All rights reserved.