Synthesis, characterization, anti-proliferative activity and chemistry computation of DFT theoretical methods of hydrazine-based Schiff bases derived from methyl acetoacetate and alpha-hydroxyacetophenone

摘要

In this study, the synthesized hydrazine Schiff bases belonging to methyl acetoacetate (1) and alpha-hydroxyacetophenone (2) were prepared by simple methods. In addition, FT-IR, UV-Vis, H-1 NMR, Mass spectra, along with melting point and conductivity measurements were used for the characterization of these compounds. The molecular structures of (1) and (2) were determined by single crystal X-ray diffraction technique. X-ray diffraction analysis reveals that (1) crystallizes in the orthorhombic system with Pca2(1) space group possessing a = 21.1032(12), b = 5.9061(3), c = 10.9717(7), beta = 90 degrees while compound (2) crystallizes in the monoclinic system with P2(1)/c space group and a = 7.0386(14), b = 13.275(3), c = 15.071(3), beta = 99.27(3)degrees. Also, theoretical studies were performed within the density functional theory (DFT) framework. Hydrazine compounds (1) and (2) were geometrically optimized using the B3LYP method with (6-311+G+ (d, p)) basis set. Calculated geometrical parameters exhibited a good agreement with experimental value. The optimized parameters from the DFT calculations were in line with experimentally measured Single Crystal X-ray Diffraction (SCXRD) results .The anticancer effects of the synthesized compounds were assayed using MTT assay against cancer cell lines K562 and MG63. (C) 2020 Elsevier B.V. All rights reserved.