Siti Munirah, Saharin (2012) Synthesis, characterizations and biological properties of some hydrazones and their metal complexes / Siti Munirah Saharin. Masters thesis, University of Malaya.
Abstract
The aim of the project as presented in this thesis concerns on the preparation, characterization and biological evaluation of Schiff bases derived from 3, 5- dihyroxybenzohydrazide and their Cu(II) and Zn(II) complexes. The Schiff bases were synthesized by the condensation of 3, 5-dihyroxybenzohydrazide and hydroxyacetophenone (BzyHAP-H), 5-bromo hydroxyacetophenone (BzyHAP-Br), 5- chloro hydroxyacetophenone (BzyHAP-Cl), salicylaldehyde (BzySAL-H), 5-bromo salicylaldehyde (BzySAL-Br), and 5-chloro salicylaldehyde (BzySAL-Cl). The BzyHAP series ligands were subsequently reacted with the acetate of Zn(II) whereas the BzySAL series ligands were reacted with Cu(II) and Zn(II) acetate in a 1:2 metal to ligand ratio. The chemical structures of the compounds were characterized by means of elemental analyses, , and spectroscopy methods including IR, 1H NMR, 13C NMR, and UV-Vis.The determination of metal content was carried out using atomic absorption spectroscopy. Single X-ray diffraction data collection is carried out for ligand BzySAL-Br. From the structural analysis, the ligand is found to be planar with an r.m.s. deviation for the non-H atoms of 0.16Å. In the crystal structure, the Schiff base molecules and the water molecules are linked together by intermolecular N-H--O and O-H--O hydrogen bonds, leading to layers parallel to the bc plane. An intramolecular O-H--N hydrogen bond involving the imine N atom and a hydroxyl substituent is also observed. The synthesized Schiff base and their metal complexes are screened for the in vitro cytotoxicity towards prostate cancer cell line (PC-3), colon cancer cell line (HT-29) lung cancer cell line (A549), and normal cell line (WRL-68). All Zn (II) complex Schiff bases show relatively low cytotoxicity against all tested cell line. Complexes labeled as CuBzySAL-H, CuBzySAL-Br, and CuBzySALCl show encouraging value of EC50 against colon cancer cell line (HT-29), lung cancer cell line (A549), and normal cell line (WRL-68). On contrary, the cytotoxicity against prostate cancer cell line (PC-3) is recorded negative. The evaluation of antioxidant reveals that all compounds are moderate DPPH inhibitor compared to the standard vitamin C.
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