Issue 3, 2012

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Abstract

Examining advances in the class of natural and non-natural piperidine azasugars, important therapeutic agents and potent glycosidase inhibitors, this review looks at syntheses applying olefin metathesis as a highly efficient key step and gateway strategy for discovery of better iminosugar leads for treatment of widespread affections like viral and metabolic diseases. Amply illustrated is how ring-closing metathesis (RCM and RCEYM), promoted by commercial ruthenium alkylidene catalysts, manage to construct the common tetrahydropyridine core while cross-metathesis (CM), starting from this generic scaffold, provides general access to families of novel azasugars. Special consideration is given to high-profile iminosugar drugs of this class (1-deoxynojirimycin and congeners, adenophorine, fagomine, isofagomine and some of their N- and C-substituted analogues) stressing upon newest trends for enhancing biological activity and modulating previously unexploited targets in multispecific therapies.

Graphical abstract: Targeted drugs by olefin metathesis: piperidine-based iminosugars

Article information

Article type
Review Article
Submitted
17 Okt. 2011
Accepted
19 Okt. 2011
First published
30 Nov. 2011

RSC Adv., 2012,2, 719-736

Targeted drugs by olefin metathesis: piperidine-based iminosugars

I. Dragutan, V. Dragutan and A. Demonceau, RSC Adv., 2012, 2, 719 DOI: 10.1039/C1RA00910A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements