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

Abstract

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 ZChO
Maciej Malinowski,,
- Department Of Organic Chemistry
, Tomasz Rowicki ZChO
Tomasz Rowicki,,
- Department Of Organic Chemistry
, Patrycja Guzik ZChO
Patrycja Guzik,,
- Department Of Organic Chemistry
, Monika Wielechowska ZTiBSL
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Anna Sobiepanek ZTiBSL
Anna Sobiepanek,,
- Department Of Drug Technology And Biotechnology
, Wojciech Sas ZChO
Wojciech Sas,,
- Department Of Organic Chemistry
Journal seriesEuropean Journal of Organic Chemistry, ISSN 1434-193X [1099-0690]
Issue year2016
Vol2016
No21
Pages3642-3649
Publication size in sheets0.5
DOIDOI:10.1002/ejoc.201600459
URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600459/full
Languageen angielski
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Score (nominal)35
ScoreMinisterial score = 35.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.834 (2) - 2016=2.762 (5)
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