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Current Topics in Medicinal Chemistry

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ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

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Recent Syntheses and Biological Activity of Lentiginosine and its Analogues

Author(s): Franca M. Cordero, Donatella Giomi and Alberto Brandi

Volume 14, Issue 10, 2014

Page: [1294 - 1307] Pages: 14

DOI: 10.2174/1568026614666140423113226

Price: $65

Abstract

(+)-Lentiginosine, a natural trans-1,2-dihydroxyindolizidine belonging to the class of iminosugars, is a potent inhibitor of amyloglucosidase, and a good inhibitor of Hsp90. The non-natural enantiomer, (–)-lentiginosine, induces apoptosis on tumor cells of different origin and is poorly cytotoxic towards non-transformed cells. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review is an update of a previous survey and summarizes the most recent achievements on biological studies as well as total syntheses of lentiginosine and trans-1,2-dihydroxyindolizidine analogues.

Keywords: Alkaloids, apoptosis, azaheterocycles, glycosidase inhibitors, hydroxyindolizidines, iminosugars, organic syntheses.

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