Diversity-Oriented Synthesis and Biological Evaluation of Iminosugars from Unprotected 2-Deoxy-D-ribose
Maciej Malinowski , Tomasz Rowicki , Patrycja Guzik , Monika Wielechowska , Anna Sobiepanek , Wojciech Sas
AbstractAn exceptionally short synthesis of novel indolizidine-,quinolizidine-, and piperidine-based iminosugars from unprotected2-deoxy-D-ribose by intramolecular 1,3-dipolar cycloaddition of sugar-derived N-(3-alkenyl)nitrones has been accomplished. The use of the 2-deoxy carbohydrate also enabled us to confirm the previously proposed mechanism for the alteration of the stereochemical course of the intramolecular 1,3-dipolar cycloaddition observed for an unprotected sugar-derived nitrone. Biological assays of the six new iminosugars revealed a slight inhibition activity of the indolizidine derivative 7a, whereas, interestingly, the two quinolizidine iminosugars 5a and 5b appeared to be weak glycosidase activators.
|Journal series||European Journal of Organic Chemistry, ISSN 1434-193X, [1099-0690]|
|Publication size in sheets||0.5|
|Score|| = 35.0, 17-08-2020, ArticleFromJournal|
= 35.0, 17-08-2020, ArticleFromJournal
|Publication indicators||= 8; = 9; : 2016 = 0.69; : 2016 = 2.834 (2) - 2016=2.762 (5)|
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