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¿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.
Appears in Collections:(IIQ) Comunicaciones congresos
(IPBLN) Comunicaciones congresos
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