Title:Structural Elucidation, In vitro and In silico Biological Evaluations of New
Fluorinated Chalcone Derivatives for Potential Antioxidant Activity
Volume: 20
Issue: 12
Author(s): Rineswary Rajasagaran, Ahmad Saifuddin Mohamad Arshad, Juzaili Azizi, Siti Nabilla Aliya Mohd Nizar and Suhana Arshad*
Affiliation:
- X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia
Keywords:
Claisen Schmidt, single crystal diffraction, antioxidant, DPPH, molecular docking, ADMET.
Abstract: The newly synthesized fluorinated chalcone derivatives are observed to possess antioxidant
potential. Two new fluorinated chalcone compounds were effectively synthesized using the Claisen-
Schmidt condensation reaction and were recrystallized using the slow evaporation method. The single
crystal structure of the compounds was determined and refined through the X-ray single crystal diffraction
method. All compounds were subjected to computational structural characterization and
Hirshfeld surface analysis. The compounds were then further characterized through the Ultravioletvisible
(UV-Vis) spectroscopic study. The chalcone derivatives were further analysed with biological
experimentation and simulation such as in vitro antioxidant (DPPH) assay, molecular docking and in
silico ADMET study. The crystal packing revealed that the molecules in the compounds were linked
together through the intermolecular C—H···O and C—H···π interactions. Hirshfeld surface analysis
validated the presence of intermolecular interactions in crystal packing. The UV-Vis spectroscopic
study revealed that the absorption wavelength of the compounds that range from 421.79 to 428.98 nm
was within the visible region with the energy gap value of 2.58 to 2.62 eV. The DPPH assay disclosed
weak antioxidant activity of both compounds (-31 to 20 %, 10000 μg/mL) compared to the standard
ascorbic acid (94.5 %, 50 μg/mL). The binding energy of the docked complex inside the target protein,
2CAG was within the range of -7.3 to -7.5 kcal/mol. In the silico model, SwissADME predicted
that the two compounds have overall good drug-like properties. Different substituents, more planar
configuration and high intramolecular interactions in the crystal packing played their role in increasing
the antioxidant activities, binding energy and drug likeliness of the synthesized compounds.
