Synthesis, characterization, antioxidant evaluation, molecular docking and density functional theory studies of phenyl and naphthyl based esters

• Published in: Journal of molecular structure 2020-05, Vol.1207, p.127812, Article 127812
• Main Authors: Zaib-un-Nisa, Shabbir, Muhammad, Akhter, Zareen, Asghar, Muhammad Adeel, Mckee, Vickie, Sani, Asma, Liaqat, Faroha, Kalsoom, Saima, Sabir, Shaista, Ismail, Hammad
• Format: Article
• Language: English
• Subjects: AIM analysis; Density functional theory; DPPH free radical activity; Esters; Hydrogen peroxide activity; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.127812

Two phenol based esters phenyl benzoate (OE1) and 1-naphthyl benzoate (OE2) were synthesized from phenol/1-naphthol and benzoyl chloride respectively. The structural elucidation of the synthesized compounds was accomplished by spectroscopic studies (FTIR, 1H NMR & GC-MS) and single crystal X-ray diffraction analysis. DPPH (2, 2-diphenyl-1-picryl-hydrazyl-hydrate) free radical and hydrogen peroxide activities were performed to evaluate the antioxidant capabilities of the synthesized esters. The compounds (OE1 & OE2) showed DPPH scavenging activity in concentration dependent manner with IC50 values 605.6 μM and 1138.7 μM correspondingly. Similarly, in hydrogen peroxide assay, OE1 and OE2 exhibited moderate activity with IC50 values 1510.2 μM and 1069.4 μM respectively. Molecular docking of the compounds was carried out to predict their antioxidant binding mechanism against target protein using the MOE suite. The structure−activity relationship analysis showed that replacing the phenyl ring by naphthyl significantly influences their activity. Geometrical studies of the compounds have been performed by both semi-empirical and DFT methods; results reveal an excellent convergence of experimental and theoretical structural parameters. A detailed bonding investigation of each compound has been performed by NBO and Bader’s AIM analysis to obtain inter and intramolecular interactions. [Display omitted] •Synthesis and characterization of phenol-based esters.•DPPH free radical and hydrogen peroxide antioxidant activities revealed their concentration dependent behaviour.•Molecular docking depicted their good antioxidant binding against target protein.•DFT studies demonstrated coherence between experimental and theoretical structural parameters.