Synthesis And Biological Activity Of Beta Amino Porphyrin Derivatives

In this paper,according to the method of Alder,5,10,15,20-tetraphenyl porphyrin was synthesized with raw materials of the distillation of pyrrole and benzaldehyde,the optimum reaction conditions in every steps were discussed in the process of ?-nitro 5,10,15,20-tetraphenyl porphyrin synthesis,and on this basis,?-amino-5,10,15,20-tetraphenyl porphyrin and metal complexe were prepared,and then oxazine ring structure of porphyrin photosensitizer were synthesized in the prence of ?-naphthol,formaldehyde;Intermediates and target products were characterized through hydrogen nuclear magnetic resonance(NMR)spectra,mass spectrum,infrared spectrum;electrochemical properties were studied by ultraviolet-visible spectroscopy,fluorescence spectroscopy,cyclic voltammetry;And biological activity of the target product was tested through the determination of singlet oxygen,gel electrophoresis method,ultraviolet visible spectrum titration method,fluorescence spectrum titration.The main work of this dissertation was composed as follows:(1)According to the method of Alder,5,10,15,20-tetraphenyl porphyrin was synthesized with raw materials of the distillation of pyrrole and benzaldehyde,propionic acid as solvent.(2)Center core metal ligand 5,10,15,20-(copper)tetraphenyl porphyrin was prepared with 5,10,15,20-tetraphenyl porphyrin and Cupric Acetate Monohydrate in solvent of N,N-dimethyl formamide.(3)5,10,15,20-(copper)tetraphenyl porphyrin was taken as starting meterials to react with acetic acid,acetic anhydride,copper nitrate in the solvent of chloroform,?-nitro-5,10,15,20-(copper)tetraphenyl porphyrin was synthesized.(4)?-nitro-5,10,15,20-(copper)tetraphenyl porphyrin was taken as raw material to react with sulfuric acid to get ?-nitro-5,10,15,20-tetraphenyl porphyrin.(5)?-nitro porphyrins as raw materials reacting with stannous chloride to get a beta-amino-5,10,15,20-tetraphenyl porphyrin.(6)?-amino-5,10,15,20-(copper)tetraphenyl porphyrin was synthesized with ?-amino-5,10,15,20-tetraphenyl porphyrin as raw material reacting with copper acetate.(7)The ?-amino copper-5,10,15,20-tetraphenyl porphyrin was taken as raw material to react with formaldehyde and ?-naphthol,porphyrin metal compounds with oxazine ring structure was prepared;And then porphyrin metal compounds with oxazine ring structurewas obtained.(8)Target products were characterized through hydrogen nuclear magnetic resonance(HNMR)spectra,mass spectrum,infrared spectrum.(9)Electrochemical properties were studied by ultraviolet-visible spectroscopy,fluorescence spectroscopy.(10)1,3-Diphenylisobenzofuran as active oxygen scavenger,in the light intermediates and target producted singlet oxygen ability using spectrophotometry,oxazine ring structure of porphyrin compounds has better ability in singlet oxygen generated.(11)With the gradient gel electrophoresis method,different concentration of porphyrin compounds cutted action of pBR322 plasmid DNA in dark and light;oxazine ring structure of porphyrin compounds have good cutting the ability of plasmid DNA.(12)Porphyrin compounds with calf thymus DNA binding ability and the interaction model were studied by ultraviolet-visible spectrometry.(13)Porphyrin compounds with calf thymus DNA binding ability and interaction patterns were studied by fluorescence spectrometry.