Synthesis of biologically active iminosugars using unconventional methods - microwave and ultrasonic irradiation
Iminosugars or azasugars are carbohydrate analogs in which the ring oxygen has been replaced with nitrogen and are found to be widespread in plants and microorganisms. They are potent inhibitors of many carbohydrate-processing enzymes involved in biological systems.
These unique molecules promise a new generation of iminosugar-based medicines for a wide range of diseases such as viral infections, diabetes, tumor metastasis, AIDS and lysosomal storage disorders. Recently it was found that iminosugars are promising immunosuppressive agents.
The synthesis of pyrollidine iminosugars and their N-alkylated derivatives is challenging from the synthetic point of view. The use of unconventional methods with ultrasonic and/or microwave activation is expected to improve yields and stereoselectivity and to lower reaction times allowing the synthesis of libraries of such compounds with different stereochemistry which can be subsequently tested as glycosidase inhibitors.
As glycosidase plays a major role in controlling the structure and function of carbohydrates at the cell surface, it is expected that the new synthetic and biological data obtained during this project will contribute to the development of new antiviral, anti infectious or anti-cancer agents.