Investigation On Syntheses, Structures And Properties Of N-arylphthalimidino Derivatives

In recent years, phthalimidino and its derivatives have attracted a great deal of interest due to their unique photophysical and biological properties. One of the significance of the synthesis of this kind of compound lies in the possibility that the new phthalimidine derivative might be a precursor of efficacious drug for therapeutic and prophylactic use. However, the majority of reported synthetic N-substituted derivatives are N-alkylphthalimidines, and most of them display no antifungal activity. Thus, a further study regarding the synthesis, bioeffect and structure-activity relationship of this kind of compound is essential.In this thesis, the current research on the structure, synthesis, properties and application of phthalimidino derivatives is reviewed. With phthalimidino ring as the nucleus, the following four N-arylphthalimidino derivatives and a related cobalt (â…¡) complex were synthesized by conventional solution reaction and hydrothermal reaction methods:2-(1-oxo-1H-2, 3-dihydro-isoindole-yl)benzoic acid(o-Hpba),3-(1-oxo-1H-2,3-dihydro-isoindole-yl)benzoic acid(m-Hpba),4-(1-oxo-1H-2,3-dihydro-isoindole-yl)benzoic acid(p-Hpba),2-hydroxyl-4-(1-oxo-1H-2,3-dihydro-isoindole-yl)benzoicacid(plp) and tri(2-(1-oxo-1H-2,3-ihydro-isoindole-yl)benzoato)-triaqua-cobalt(â…¡)-sodium)(â… )(NaCo(H2O)3(o-pba)3). All these compounds were fully characterized by elemental analysis, IR and 1H NMR spectroscopy, and high resolution mass spectrometry, et al.Synthesis method of the above-mentioned compounds was systematically elucidated. A new binary schiff base intermediate (C6H4(CH=NC6H4COOH)2) was observed during the study of the mechanism of the key cyclization reaction of o-phthalaldehyde with primary amine compounds, which indicated a new mechanism similar but slightly different to those reported in recent literatures.An experimental research was carried out towards the single crystal of o-Hpba, p-Hpba and NaCo(H2O)3(o-pba)3, and it showed that the oxidation process of cuprous halide played a crucial role in the crystal growth of the former two. Based on this finding, we proposed a total new method for the crystallization of organic compound, namely nonself reaction-induced crystallization. The crystal structures of these three compounds were carefully determined by single crystal and powder X-ray diffraction techniques. The complex NaCo(H2O)3(o-pba)3 gave rise a new type of meso-one-dimensional syndiotactic coordination polymer.The fluorescence properties of all synthetic compounds were studied. Experimental results showed that the emission intensity was affected by the substitution position of the carboxylate group on its N-connected benzene ring, and the ortho and para substituted materials have strongest blue fluorescence emissions. The inhibition of four ligands against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Candida albicans had been evaluated by the minimum inhibition concentration (MIC) test using the doubling-dilution method. All ligands were found to display a broad-spectrum inhibitory activity against these representative strains of Gram-negative bacteria, Gram-positive bacteria and fungus, and the inhibition efficiency was dependent somewhat on the substitution position of N-substituted benzene ring, among which the compound with substituent on the meta-position is more active than the others. It might provide an experimental and theoretical basis for further design and synthesis of new bioactive phthalimidino derivatives and lead compounds of pharmaceuticals.