Synthesis Of Dehydroabietyl-1, 3, 4-oxadiazole Derivatives And Their Interactions With DNA

In recent years, compounds containing nitrogen attract great interest in the development of life science. There're a lot of synthesis medicines and lots of natural products like alkaloids, some vitamins and antibiotics containing nitrogen. They are not only used widely in herbicides, insecticide, fungicide but also play important role in dyes, sensitive materials, surfactants and functionally materials. Oxadiazole derivatives are important compounds containing nitrogen. So the synthesis and properties of these compounds are promising in future.Dehydroabietic acid is one of important renewable resource. It is widely used in many fields such as paint, adhesives, printing ink, papermaking, rubber, etc. Like some natural drugs, it has an aromatic diterpene structure with three rings. It also has three chiral carbon atoms and a reactive carboxy group. So it might be hopefully modified to some multifunctional derivatives which can be used as high added value products like novel fluorescence derivative reagents, efficient low toxic medicines by constructing aromatic or heteroaromatic ring on its skeleton. It not only meets with the demand of green chemistry but also bring about favorable economical and social effects.There are three parts in this dissertation. Part I, starting from dehydroabietic acid which was purified disproportionated rosin, Compounds 4 were prepared by the reaction of aromatic aldehydes with dehydroabietic acyl hydrazine 3, and 5 was obtained from the reaction of 4 with iodosobenzene diacetate. The structures of the title compounds were confirmed by IR, 1H NMR and 13C NMR; We study on the ultraviolet and fluorescence properties of title compounds.Part II, crystalline inclusion coumpounds of 4a, 4b, 4d was prepared and confirmed by means of IR and powder XRD. The host-guest molar ratio was determined by 1H NMR. The X-ray diffraction inclusion compounds of 4a·C2H5OH and 4b·C2H5OH showed that their crystal belong to orthorhombic, space group P2(1)2(1)2(1). These inclusion compounds exhibit O2—H2…O1, N1—H1…O2, O2—H2…N2 hydrogen bonding interactions, guest molecules were filled in a proper manner in the tunnel formed by host molecules.Part III, the interaction between 5d, 5h, 5j, 5k with ct-DNA was studied by fluorescence spectra .5d, 5h, 5k can react with ct-DNA except 5j. The flourescence intensity of DNA-5k enhanced with the increasing of the DNA gradually, and the result of 5d, 5h with ct-DNA is fluorescence quenching. They belong to static quenching, and the binding constant for 5d, 5h with ct-DNA are 3.75×103 L·mol– 1, 8.64×103 L·mol– 1. The interaction between other title compounds and ct-DNA are undergoing.In summary, in this dissertation, 25 new compounds were synthesized and characterized by IR, NMR, etc. Study on the inclusion capability of 4a, 4b, 4d, and the interaction between 5d, 5h, 5j, 5k with DNA was studied by fluorescence. Our study shows that the exploition of multifunctional reagents through constructing heteroaromatic ring on the skeleton of dehydroabietic acid laid the groundwork for future. the bioactivities are undergoing.