Naturally Occurring Iminosugars and Related Alkaloids: Structure, Activity and Applications

Asano, Naoki

doi:10.1002/9780470517437.ch2

Cited by 7 publications

(2 citation statements)

References 104 publications

(156 reference statements)

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“…1) [29][30][31][32][33][34][35]. Such substitution enables not only monocyclic but also bicyclic scaffolds and while the synthetic analogues may be represented by numerous ring forms, the naturally occurring iminosugars are classified into five structural classes: pyrrolidines, piperidines, indolizidines, pyrrolizidines and nortropanes (Fig.…”

Section: Iminosugars: Classification Occurrence and Historical Contextmentioning

confidence: 99%

Iminosugars: Therapeutic Applications and Synthetic Considerations

Horne

2014

Topics in Medicinal Chemistry

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Iminosugars, carbohydrate mimetics in which the endocyclic oxygen of the parent carbohydrate is replaced with nitrogen, are the most important class of carbohydrate mimetic reported to date with two marketed drugs and several in clinical development. Since their first isolation in the 1960s iminosugars have captured the imagination of both synthetic and medicinal chemists alike with recent therapeutic developments highlighting the need for improved routes of synthesis. The resurgence in the therapeutic application of iminosugars has arisen as a consequence of our growing understanding on the role that glycobiology plays in disease and development. There are myriad possible individual targets encompassing a range of therapeutic areas, all of which can potentially be addressed by iminosugars. This chapter presents the historcial development of this compound class before discussing some of the issues that iminosugars present as synthetic targets. The therapeutic potential of this class of compound with specific reference to the development of modulators of glucocerebrosidase activity is discussed.

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Section: Iminosugars: Classification Occurrence and Historical Contextmentioning

confidence: 99%

Iminosugars: Therapeutic Applications and Synthetic Considerations

Horne

2014

Topics in Medicinal Chemistry

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“…A large diversity of 1-deoxyiminosugars was found a posteriori in microorganisms and plants [e.g., DMDP (2,5-dihydroxymethyl-3,4dihydroxypyrrolidine also known as 2,5-dideoxy-2,5-imino-D-mannitol), Figure 1] [3] and many new structures synthesized [4]. The biological studies on these compounds revealed their remarkable properties as inhibitors of glycosidases, as well as of other carbohydrate-processing enzymes [5]. When protonated, they mimic charge and shape of the cationic intermediates generated in the glycosidase catalyzed reactions.…”

Section: Introductionmentioning

confidence: 99%

A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

Jaszczyk

Cocaud

et al. 2019

Carbohydrate Research

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Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

Jung

Lee

2014

Asian J Org Chem

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Chiral aziridine-2-carboxylates have two important functional groups, the carboxylate group and aziridine ring, that are useful for synthetic purposes. As both (2R)-and (2S)-aziridine-2-carboxylates were commercialized in optically pure forms, we have studied to extend their synthetic utilities for the construction of various nitrogen-containing molecules. The C2 ester group can be transformed into aldehydes, alcohols, amides, ketones, b-ketoesters, and amines bearing diverse substituents with defined stereochemistry in high yields. In particular, ring-opening reactions of aziridines are carried out in regio-and stereoselective manners toward a-or b-amino cyclic and acyclic compounds in optically pure forms. The highlight of this chemistry based on the regio-and stereoselective functional-group transformations of aziridine-2-carboxylates is exemplified by efficient and highly stereoselective syntheses of many biologically important amines, including natural products.

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Naturally Occurring Iminosugars and Related Alkaloids: Structure, Activity and Applications

Cited by 7 publications

References 104 publications

Iminosugars: Therapeutic Applications and Synthetic Considerations

Iminosugars: Therapeutic Applications and Synthetic Considerations

A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

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