Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp²-Iminosugar Glycolipids.

ABSTRACT: The unique stereoelectronic properties of sp²-iminosugars enable their participation in glycosylation reactions, thereby behaving as true carbohydrate chemical mimics. Among sp²-iminosugar conjugates, the sp²-iminosugar glycolipids (sp²-IGLs) have shown a variety of interesting pharmacological properties ranging from glycosidase inhibition to antiproliferative, antiparasitic, and anti-inflammatory activities. Developing strategies compatible with molecular diversity-oriented strategies for structure-activity relationship studies was therefore highly wanted. Here we show that a reaction sequence consisting in stereoselective C-allylation followed by thiol-ene "click" coupling provides a very convenient access to α-C-glycoside sp

SUBMITTER: Sanchez-Fernandez EM 

PROVIDER: S-EPMC6720825 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature