Study On Syntheses, Characterization And Property Of Organoantimony Derivatives From Aryl Aldehyde Amine Complexes Of Schiff Bases

Organoantimony compounds have received increasing attention owing to their bioactivities, in particular as potential biocidal and anticancer agents in pharmaceutical, inorganic and medicinal chemistry. Organoantimony schiff compounds appeared to exhibit potent antitumour activities, in some cases being more effective than cisplatin in vitro antitumour tests. For these reasons, the relationship between the structural features of organoantimony schiff compounds and the antitumour activities has also become a research hotspot. Considering the above circumstances, we took a systematic study on the syntheses of the organoantimony schiff compounds. We have characterized them with the measure of melting point elemental analysis, NMR spectra analysis, IR and X-ray single crystal diffraction analysis. And we doped out the processes and the formation mechanism of the product based on the analysis of the structure of the compounds. The main work can be described as follows:1. In this article, we have successfully prepared three schiff ligands and three novel organoantimony metal complexes: tris(3-fluorophenyl)antimony dichlorides, tris(4-fluorophenyl)antimony dichlorides and tris(3,4,5-trifluorophenyl)antimony dichlorides. We have characterized them with the X-ray single crystal diffraction.2. Studies on the synthesis, structural characterization, in vitro cytotoxicities and DNA interaction of organoantimony compounds with(Z)-3-(2-hydroxybenzylideneamino)benzoic acid. Four compounds have been obtained and characterized by elemental analysis, melting point, FT-IR, NMR, and X-ray single crystal diffraction. The results show that the structures are similiar when the ligand reacts with Triphenylantimony dichloride, tris(3-fluorophenyl)antimony dichlorides and tris(4-fluorophenyl)antimony dichlorides with the central antimony atom five-coordinated( trigonal bipyramidal); the reaction with tris(3,4,5-trifluorophenyl)antimony dichlorides obtains a octahedral geometry. Preliminary in vitro cytotoxicity studies on four human tumor cells lines(HL-60, A549, HCT-116 and Hela) by MTT assay reveal that mono-fluoro-substituted complexes exhibit good in vitro cytotoxicities toward the four cell lines. The DNA-binding properties of complexes with calf thymus DNA(CT-DNA) have also been investigated by fluorescent spectra and UV spectra. The results confirm that the organoantimony complexes binds to CT-DNA in an intercalative mode.3. Studies on the synthesis, structural characterization, in vitro cytotoxicities and DNA interaction of organoantimony compounds with(Z)-3-(2-hydroxy-3-methoxybenzylideneamino)benzoic acid. Four compounds have been obtained and characterized by FT-IR, elemental analysis, melting point, NMR, and X-ray single crystal diffraction. The results show that the structures are similiar when the ligand reacts with Triphenylantimony dichloride, tris(3-fluorophenyl)antimony dichlorides and tris(4-fluorophenyl)antimony dichlorides with the central antimony atom five-coordinated( trigonal bipyramidal); the reaction with tris(3,4,5-trifluorophenyl)antimony dichlorides obtains a octahedral geometry. Preliminary in vitro cytotoxicity studies on four human tumor cells lines(HL-60, A549, HCT-116 and Hela) by MTT assay reveal that mono-fluoro-substituted complexes exhibit good in vitro cytotoxicities toward the four cell lines. The DNA-binding properties of complexes with calf thymus DNA(CT-DNA) have also been investigated by fluorescent spectra and UV spectra. The results confirm that the organoantimony complexes binds to CT-DNA in an intercalative mode.4. Studies on the synthesis, structural characterization, in vitro cytotoxicities and DNA interaction of organoantimony compounds with(Z)-2-chloro-5-(2-hydroxybenzylideneamino)benzoic acid. Four compounds have been obtained and characterized by FT-IR, elemental analysis, melting point, NMR, and three of them have been characterized by X-ray single crystal diffraction. The results show that the structures are similiar when the ligand reacts with Triphenylantimony dichloride, tris(3-fluorophenyl)antimony dichlorides and tris(4-fluorophenyl)antimony dichlorides with the central antimony atom five-coordinated( trigonal bipyramidal); Preliminary in vitro cytotoxicity studies on four human tumor cells lines(HL-60, A549, HCT-116 and Hela) by MTT assay reveal that mono-fluoro-substituted complexes exhibit good in vitro cytotoxicities toward the four cell lines. The DNA-binding properties of complexes with calf thymus DNA(CT-DNA) have also been investigated by fluorescent spectra and UV spectra. The results confirm that the organoantimony complexes binds to CT-DNA in an intercalative mode.