Iminosugars as Immunomodulating Agents: Synthesis and Biological Activities of 1‐Deoxynojirimycin and Related Compounds

Abstract

Iminosugars are an extremely interesting and versatile class of compounds and have many potential therapeutic applications. However, the use of iminosugar derivatives as immunomodulating agents is an area that is less explored. This review describes recent advances in the field of iminosugars as immunomodulating agents with a particular emphasis on 1‐deoxynojirimycin analogues and related compounds. Both chemical and biological aspects concerning their preparation and/or occurrence in nature, as well as their immunomodulatory properties, are discussed.

Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis

“…Over the last decades, iminosugars have become the most popular class of carbohydrate-processing enzyme modulators, being able to alter the glycosylation profile of eukaryotic cells, to interfere in carbohydrate and glycoconjugate metabolism, to regulate the folding and transport of glycoproteins, and to stop the interaction mediated by host cell carbohydrates with infective agents. All these abilities allowed relevant applications of these small molecules as immune system modulators [21][22][23], anti-cancer agents [24] and as therapeutic agents for the treatment of lysosomal storage disorders [25][26][27][28][29], a group of more than 50 rare disorders caused by specific mutations in genes encoding lysosomal enzymes and transporters.…”

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

“…Several other Figure 1. Selected naturally occurring compounds with a polyhydroxylated piperidine (with at least three OH in ring) See references [16][17][18][19][20][21][22][23][24][25][26][27][28].…”

“…[14] These are for the treatment of various disease such as cancers, viral infections (Dengue, HIV), and cystic fibrosis. [9,15] Iminosugars have also been investigated as immunomodulators, [16] as activity based molecular probes, [17] or in peptidomimetic research. [18] Recently an argument was made for repurposing of miglitol, celgosivir and miglustat for the treatment of COVID-19.…”

A Route to 1‐Deoxynojirimycin and 1‐Deoxymannojirimycin Derivatives with Quaternary Centers Adjacent to the Ring Nitrogen from Methyl α‐d‐Mannopyranoside

“…It can be envisaged that new imino sugars with quaternary centers can be of interest in drug discovery as glycosidase inhibitors, as immunological modulators, as activity based probes or to be used in peptidomimetic research, given they have found applicability as scaffolds in that area . Despite a sustained interest in discovery of drugs based on glycomimetics,, there have been only a few syntheses of imino sugars with quaternary centers.…”