Saliha Saouli, I. Selatnia, B. Zouchoune
Aug 5, 2020
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Influential Citations
19
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Journal
Journal of Molecular Structure
Abstract
Abstract An aromatic α, β-unsaturated Ketone (2E,5E)-2,5 bis(4-isopropyl benzylidene) cyclopentanone (A) have been achieved by a Claisen-Schmidt reaction. A new hydrazone derivative 1-(2,5-bis((E)-4-isopropyl benzylidene) cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine (B) was synthesized by reacting under reflux chalcone (A) with 2,4-dinitrophenylhydrazine and evaluated for its biological activities. The structure of the title compound (B) was studied using different spectroscopic techniques such as 1H and 13C NMR, FT-IR, UV–visible and confirmed by low-temperature single-crystal X-ray diffraction analysis. Complementary computation studies using DFT and TD-DFT at B3LYP reproduced well the experimental geometrical parameters and the spectroscopic properties. The obtained biological results revealed that the synthesized compound displayed higher antioxidant activity (IC50 = 6.95 ± 0.03 μM) in comparison to BHA and BHT standards by superoxide anion radical assay, and an interesting anti-tyrosinase activity (IC50 = 15.84 ± 1.10 μM), approximately 2-fold more than that of Kojic acid which was used as a reference.