Iminosugars and Relatives as Antiviral and Potential Anti-infective Agents

Abstract

Iminosugars have emerged in the literature during mid-1960's as synthetic compounds. Around the same time, the first examples were found in Nature and their interesting enzyme inhibitory properties were recognised. Due to their powerful interference with glycohydrolases (glycosidases) as well as glycosyltransferases, quite a few representatives exhibit notable biological activities. These range from anti-diabetic, insect antifeedant, nematicidal, plant growth regulating to immunomodulating, anti-cancer as well as - in selected cases - anti-infective properties. The latter will be the focus of the following survey.

Molecular Basis for β‐Glucosidase Inhibition by Ring‐Modified Calystegine Analogues

“…[2,3] Similar to the well-studied polyhydroxypiperidine, indolizidine, pyrrolidine and pyrrolizidine-type iminocyclitols, [4] calystegines exhibit potent glycoside hydrolase (glycosidase) inhibitory properties. Given the broad range of biological events in which glycosidases are involved, inhibitors of these enzymes have potential in therapies that are targeted at, for example, cancer, [5] viral infections, [6] tuberculosis, [7] diabetes [8] and glycosphingolipid storage disorders.…”

Recent Advances in the Total Synthesis of Piperidine Azasugars

“…3-epi-Fagomine (19) and 3,4-di-epi-fagomine (20) and their glucopyranosyl derivatives were found in leaves of Xanthocercis zambesiaca (Leguminoseae) in 1997. [15] …”

Carbohydrate-based therapeutics

“…Recent targets have included amino sugars (Greimel et al 2003;Nishimura 2003), sulfated carbohydrates (e.g., salacinol) and C-linked glycosides. The latter are mimics of natural carbohydrates but offer the advantage of longer half lives under physiological conditions.…”