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Title

¿Click¿ Synthesis and Pharmacological Evaluation of sp2-Iminosugars S- and C-Glycosides

AuthorsGarcía-Moreno, M. I.; Sánchez-Fernández, E. M.; Padrón, J. M.; García-Hernández, R.; Gamarro, Francisco; García Fernández, J. M.; Ortiz Mellet, C.
Issue Date19-Feb-2020
Abstractsp2-Iminosugars are carbohydrate mimics with unique properties in terms of chemical and structural versatility. The presence of a pseudoamide nitrogen at the position of the ring oxygen in monosaccharides enables glycosidation reactions and strongly favors the ¿-orientation of glycosidic substituents by the convergence of the anomeric and steric effects. In the last years, several approaches have been explored to access sp2-iminosugar O-, N-, S-, and C-glycosides as mimetics of bioactive glycoconjugates. Thus, sp2-iminoglycolipid (sp2-IGLs) analogs of immunoregulatory glycolipids were synthesized and found to exhibit a variety of pharmacological activities against cancer,1 parasitic diseases2 and inflammatory disorders.3 In this context, we now present a molecular diversity-oriented strategy to access a-S or ¿-C sp2-IGLs in high yield and with total stereocontrol that exploit several ¿click¿ methodologies. A series of derivatives have been prepared in this manner and their glycosidase inhibitory, antiproliferative and antileishmanial activities were screened in parallel in the frame of structureactivity relationship studies.
URIhttp://hdl.handle.net/10261/215925
Appears in Collections:(IIQ) Comunicaciones congresos
(IPBLN) Comunicaciones congresos
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