(+)-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.
Recent Syntheses and Biological Activity of Lentiginosine and its Analogues / Franca Maria Cordero; Donatella Giomi; Alberto Brandi. - In: CURRENT TOPICS IN MEDICINAL CHEMISTRY. - ISSN 1568-0266. - STAMPA. - 14:(2014), pp. 1294-1307. [10.2174/1568026614666140423113226]
Recent Syntheses and Biological Activity of Lentiginosine and its Analogues
CORDERO, FRANCA MARIA;GIOMI, DONATELLA;BRANDI, ALBERTO
2014
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.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.