Issue 3, 2012
From the journal:

RSC Advances

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Ileana Dragutan,*a   Valerian Dragutana  and  Albert Demonceaub  

* Corresponding authors

a Institute of Organic Chemistry, Romanian Academy, 202B Spl. Independentei, P.O. Box 35-108, Bucharest, Romania
E-mail: idragutan@yahoo.com

b Macromolecular Chemistry and Organic Catalysis, Institute of Chemistry (B6a), University of Liège, Sart Tilman, Liège, Belgium

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

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Article information

DOI
https://doi.org/10.1039/C1RA00910A
Article type
Review Article
Submitted
17 Oct 2011
Accepted
19 Oct 2011
First published
30 Nov 2011

RSC Adv., 2012,2, 719-736

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Targeted drugs by olefin metathesis: piperidine-based iminosugars

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

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