Computational modeling of imines based anti-oxidant and anti-esterases compounds: Synthesis, single crystal and In-vitro assessment

Raza M. A., Farwa U., Danish M., Öztürk S., Aagar A. A., DEGE N., ...More

COMPUTATIONAL BIOLOGY AND CHEMISTRY, vol.104, 2023 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 104
  • Publication Date: 2023
  • Doi Number: 10.1016/j.compbiolchem.2023.107880
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, BIOSIS, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, Computer & Applied Sciences, EMBASE, INSPEC, MEDLINE, zbMATH
  • Keywords: Molecular docking, Imines, Single crystal X-Ray diffraction, Density functional theory, Hirshfeld surface analysis, ANHARMONIC COUPLING THEORY, HIRSHFELD SURFACE-ANALYSIS, IR SPECTRAL DENSITY, H-BONDS, MOLECULAR DOCKING, FERMI RESONANCES
  • Ondokuz Mayıs University Affiliated: Yes


Molecular modeling strategy was adopted to check the biological potential of the imine based molecules against free radical, acetylcholine esterase and butyrylcholine esterase. Three Schiff based compounds as (E)- 2-(((4- bromophenyl)imino)methyl)-4-methylphenol (1), (E)-2-(((3-fluorophenyl)imino)methyl)-4-methylphenol (2) and (2E,2E)-2-(2-(2-hydroxy-5-methylbenzylidene)hydrazono)-1,2-diphenylethanone (3) were synthesized with high yield. The synthesized compounds were characterized with the help of modern techniques such as UV, FTIR and NMR while exact structure was depicted with Single Crystal X-Ray diffraction technique which dis-closed that compound 1 is orthorhombic, while 2 and 3 are monoclinic. A hybrid functional (B3LYP) method with general basis set of 6-31 G(d,p) were applied to optimize synthesized Schiff bases. The contribution of in-between molecular contacts within a crystalline assembly of compounds were studied using Hirshfeld surface analysis (HS). In order to check the ability of the synthesized compounds toward free radical and enzyme in-hibition, in vitro models were used to assess the radical scavenging and enzyme inhibition potential which depicted that compound 3 showed highest potential (57.43 +/- 1.0%; DPPH, 75.09 +/- 1.0%; AChE and 64.47 +/- 1.0%; BChE). The ADMET assessments suggested the drug like properties of the synthesized compounds. It was concluded from results (in vitro and in silico) that synthesized compound have ability to cure the disorder related to free radical and enzyme inhibition. Compound 3 was shown to be the most active compared to other compounds.