Biological Eveluation And Synthesis Of1,3,4-Oxadiazolines Drived From1,4:3,6-dianhydro-D-fructose

Oxadiazolines are an important class of heterocyclic compounds which havemany biological activities and have been widely used in pesticide and medicine.1,4:3,6-Dianhydro-D-fructose is an ideal starting material in chiral synthesis due to itsspecial “V-type” backbone and reactive carbonyl group. Previous studies showed thatmany1,4:3,6-dianhydro-D-fructose derivatives have obvious biological activities. Inthis thesis, A series of new oxadiazoline derivatives from1,4:3,6-dianhydro-D-fructose were synthesized and their bioactivities were evaluated primarily.1.1,4:3,6-dianhydro-D-fructose reacted with hydrazides to afford hydrazones,then the hydrazones were treated with acetic anhydride to afford1,4:3,6-dianhydro-D-fructose fused oxadiazole derivatives. This research expands the application of1,4:3,6-dianhydro-D-fructose.2. The lipid-water partition coefficient of the compounds may influence theirbiological activities by changing their penetrating abilities through the cell membraneand their binding abilities with enzyme and receptors. So some oxadiazolines withdifferent lipid-water partition coefficients were obtained by deacetylation. 3. The compounds′anti-tumour activities in vitro were carried on two kinds ofhuman cancer cell lines by using SRB assay. Experiment results show that theoxadiazolines possess week antitumor activities against human lung cancer A549cells and human gastric carcinoma MGC803cells.4. The in vitro antimicrobial activities of some synthetic oxadiazolines wereevaluated by mircrobroth dilution assay. According to the results, the testedcompounds have week antimicrobial activities against the standard strains ofStaphylococcus aureus and Escherichia coli.In this thesis,24compounds were synthesized, and20of them have not beenreported. All the compounds were characterized by1H NMR,13C NMR spectralanalysis. This work exploited new methods for synthesizing of more1,4:3,6-dianhydro-D-fructose derivatives.