Synthesis, spectroscopic characterization, crystal structure, DFT studies and biological activities of new hydrazone derivative: 1-(2,5-bis((E)-4-isopropylbenzylidene)cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine

An aromatic a, b-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, UVevisible 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 1/4 6.95 +/- 0.03 mM) in comparison to BHA and BHT standards by superoxide anion radical assay, and an interesting anti-tyrosinase activity (IC50 1/4 15.84 +/- 1.10 mM), approximately 2-fold more than that of Kojic acid which was used as a reference. (c) 2020 Elsevier B.V. All rights reserved.