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


An 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.
Author Maciej Malinowski (FC / DOC)
Maciej Malinowski,,
- Department Of Organic Chemistry
, Tomasz Rowicki (FC / DOC)
Tomasz Rowicki,,
- Department Of Organic Chemistry
, Patrycja Guzik (FC / DOC)
Patrycja Guzik,,
- Department Of Organic Chemistry
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Anna Sobiepanek (FC / IBC / DDTB)
Anna Sobiepanek,,
- Department Of Drug Technology And Biotechnology
, Wojciech Sas (FC / DOC)
Wojciech Sas,,
- Department Of Organic Chemistry
Journal seriesEuropean Journal of Organic Chemistry, ISSN 1434-193X, [1099-0690]
Issue year2016
Publication size in sheets0.5
ASJC Classification1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600459/full
Languageen angielski
wdpb_publikacje_pliki_plik_publikacja_2896_org.pdf 957.59 KB
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 17-08-2020, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 17-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 8; WoS Citations = 9; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.69; WoS Impact Factor: 2016 = 2.834 (2) - 2016=2.762 (5)
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