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Anti-oxidant behavior of functionalized chalcone-a combined quantum chemical and crystallographic structural investigation

Publication Type : Journal Article

Publisher : Journal of Molecular Structure

Source : Journal of Molecular Structure, Volume 1146, p.301-308 (2017)

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Keywords : antioxidant activity, Chalcones, crystal structure, DFT, DPPH test, H₂O₂ assay

Campus : Kochi

School : School of Pharmacy

Center : Amrita Institute of Medical Science

Department : Pharmaceutical Chemistry & Analysis

Year : 2017

Abstract : Compound (2E)-3-(methoxyphenyl)-1-(4-methylphenyl) prop-2-en-1-one (Ch) was synthesized by the Claisen-Schmidt condensation reaction between para-methylacetophenone and para-methoxybenzaldehyde under basic condition. The structure of the molecule was elucidated using X-ray diffraction. Compound (Ch) demonstrated higher antioxidant activities in the DPPH test and H2O2 assay (IC50 = 12.23 ± 0.53 and 15.62 ± 0.98) than with the standard ascorbic acid (IC50 = 17.32 ± 0.44 and 19.07 ± 0.35). An evaluation of the atomic and molecular properties of ascorbic acid and Ch were computed based on their antioxidant activities. The molecular properties give insight into possible reasons for the enhanced antioxidant properties of Ch compared to ascorbic acid. The atomic properties provide further insight into chemical changes of the atoms of the compounds. Such changes include electronic shifting of the compounds electrophilic and/or nucleophilic states which highlight chemical moieties which characterize the antioxidant activity but do not directly relate to a variation in their antioxidant activities. The results obtained reflect oxygen atoms having significant nucleophilic interactions of each of the compounds. This was characterized by higher Fukui indices, isotropic and anisotropic hyperfine and orbital coupling stability energy.

Cite this Research Publication : Bijo Mathew, Adeniyi, A. A., Joy, M., Mathew, G. Elizabeth, Singh-Pillay, A., Sudarsanakumar, C., Soliman, M. E. S., and Suresh, J., “Anti-oxidant behavior of functionalized chalcone-a combined quantum chemical and crystallographic structural investigation”, Journal of Molecular Structure, vol. 1146, pp. 301-308, 2017.

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