Iminosugars have shown great potential in pharmaceutical industry due to their potent glycosidase inhibition, anti-virus and anti-cancer activities. Systematic study of structure-activity relationship of iminosugars will help to develop highly active and selective lead compounds. Fluorination is usually the most used method of studying structure-activity relationship. This review summarized the reported synthetic strategies of fluorinated iminosugars and the related glycosidase inhibitory activities. The synthetic strategies are roughly categorized to three types, namely, fluorine containing building blocks, fluorinated sugars and fluorinating reagents, and each of them is reviewed with merits, disadvantages and its application. The structure-activity relationship of some representative iminosugars is then preliminarily concluded based on the reported glycosidase inhibitory activities of fluorinated iminosugars. Intact iminosugar ring is believed important for interaction with enzymes, while fluorination of side chain and the fused ring would influence inhibitory spectrum and potency, respectively. Therefore, the current research results of fluorinated iminosugars have made important contributions to iminosugar chemistry. With fluorine as tool, the structure-activity relationship of iminosugars can be further completed and corrected in the future, and therefore would certainly help to provide profound foundation for the design and syntheses of iminosugars with potential medicinal values, and thus effectively promote the related drug discovery.
Contents
1 Iminosugar and its application
2 Synthetic strategies of fluorinated iminosugars and related biological activity study
2.1 Synthesis of fluorinated iminosugars from fluorinated building blocks
2.2 Synthesis of fluorinated iminosugars from fluorinated sugars
2.3 Synthesis of fluorinated iminosugars by subsequent introduction of fluorine
3 Fluorination in structure-activity relationship study of iminosugars