Synthesis Of Galactosidase Inhibitors

Inhibitors of glycosidases have been attractive compounds for synthetic chemists and biochemists, not only because they serve as useful biological tools for studying the biological functions of oligosaccharides but also they may have great potential as drugs to treat a variety of carbohydrate-mediated diseases. They are now finding clinical applications as anti-HIV, anti-cancer, anti-flu and anti-diabetic agents. Therefore it's very important to synthesize glycosidase inhibitors for finding new drugs.In this thesis, the structure-activity relationships of the known glycosidase inhibitors and the typical synthetic methods of iminosugars were reviewed. Based on the transition-state of the enzyme-catalyzed reactions, some iminosugar derivatives were designed and synthesized.Utilizing the mercury acetate-mediated cyclization reaction, 3 iminosugars were isolated via 11 steps starting from galactose. The configurations of three isomers were identified using NMR technique. And then some nitrogen-substituted derivatives were prepared.36 compounds were synthesized in this thesis and 20 of them were unknown. All these new compounds were characterized by their ¹H NMR, ¹³C NMR, MS, HRMS/elemental analysis.