Synthesis And Bioactivity Study Of Dehydroabieticacyl Thiourea Compounds And Related Heterocyclic Derivatives

In recent years, compounds containing nitrogen attract great interst in the development of life science. There're a lot of synthetic 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 roles in dyes, sensitive materials, surfactants and functionally materials. Thiourea, triazole, tetrazolate and thiadiazole are important compounds containing nitrogen.Dehydroabietic acid (DAA) and Dehydroabietic amine are the isomerides in the renewable rosin. They are used widely in many fields such as paint, adhesives, printing ink, papermaking, rubber food, etc like some natural drugs, they have an aromatic diterpene structure with three rings, which also have three chiral carbon atoms and reactive carboxy group and amino group respectively. So they 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 their skeleton. It not only meets with the demand of green chemistry but also bring about favorable economical and social effects.In attempt to find novel bioactive compounds, a series of 3-substituted thiourea derivatives 4 and 5-dehydroabietyl-3-arylamino-4H-[1,2,4]triazole 5 were synthesized from dehydroabietic acid. Compounds 5 were prepared by the reaction of hydrazine hydrate with 4, and 4 was obtained from the reaction of dehydroabietic acyl isothiocyanate 3 with amines. The structures of the title compounds were confirmed by IR, 1H NMR and 13C NMR. The preliminary biological tests display that some of the title compounds (4j, 4e, 4f, 5b) posses a fungicidal activity against B. subtilis on test concentration (for 4j: 50 mg/L; for 4e, 4f, 5b: 100 mg/L); 4b, 4h, 4i, 5e posses a fungicidal activity against E. coli on test concentration (100 mg/L).And we also synthesized arene derivatives containing amide and thiourea units 6 from 3 and 4-substituted benzoylhydrazides. 6 was treated under the catalysis of glacier acetic acid giving its ring closure products 7. The preliminary biologic tests show that 6c, 6f, 7f posses a fungicidal activity against B. subtilis and E. coli. In addition, we synthesized 9 (DHA-NCS) from dehydroabietic amine. And compounds 11 were prepared by the reaction of halides with 10. Compound 10 was synthesized from 9 and sodium azide. Compound 11 exhibited no activity in the preliminary antimycobacterial activities tests against B. subtilis and E. coli.In summary, in this thesis, 36 new compounds were synthesized and characterized by IR, NMR, etc. And the preliminary antimycobacterial activities against B. subtilis and E. coli were tested. Our study shows that the exploitation of multifunctional reagents through constructing thiourea or heteroaromatic ring on the skeleton. of dehydroabietic acid and dehydroabietic amine laid the groundwork for future. Further bioactivities are undergoing.