Stereoselective synthesis and sialidase inhibition properties of KDO-based glycosyloxathiins

Abstract

The stereoselective synthesis of KDO-based glyco-1,4-oxathiins is described. Relying on a totally diastereoselective inverse electron demand hetero Diels-Alder, αα′-dioxothiones as electron-poor heterodienes, and glycals as electron-rich dienophiles, reacted to give, in high yield, the KDO-based glyco derivatives 11 and 12a-c. Taking into account their structural features, biological tests have been run to evaluate the properties of 11 and 12a as sialidase inhibitors. The synthetic and biological data reported confirmed the versatility of this powerful [4+2] cycloaddition and showed the KDO-based cycloadduct 11 as attractive scaffold for the development of new sialidase inhibitors.

Benzo[c][1,2]thiazine‐Based Analogs in the Inverse Electron Demand [4+2] Hetero Diels‐Alder Reaction with Glycals: Access to Tetracyclic Fused Galactose and Fucose Derivatives

“…compounds 1 – 4 , Figure 1). [13] The molecular mimicry properties of these molecules allowed for the investigation of the biological effect that these glycomimetics had in specific contexts where the recognition of carbohydrates plays a crucial role leading to the identification of antibacterial agents [13a,14] (compound 1 , Figure 1) inhibitors of glycosyltransferases [15] and glycosidases [13b] (compounds 1 – 2 , Figure 1), and tumor associated carbohydrate antigens [16–19] (compounds 3 – 4 , Figure 1).…”