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Preparation and Biological Evaluation of Pyrrolidinediols and Pyrrolidine N ‐Oxides from D ‐Ribose Using the Nitrone Approach
Author(s) -
Palmer Andreas M.,
Jäger Volker
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200107)2001:13<2547::aid-ejoc2547>3.0.co;2-h
Subject(s) - nitrone , chemistry , pyrrolidine , combinatorial chemistry , organic chemistry , catalysis , cycloaddition
The transformation of 3,4‐isopropylidenedioxy‐5‐methylpyrrolidine 1‐oxides with various 2‐substituents into the free diols and, by reduction, into the corresponding pyrrolidinediols (iminoglycitols) is described. The pyrrolidine N ‐oxides were derived from D ‐ribose via unsaturated hydroxylamines, with the key steps of nitrone addition and Cope−House cyclization as described earlier. The biological activity of these compounds with respect to glycosidase inhibition was examined; while all the tested pyrrolidine N ‐oxides proved inactive, some of the new iminopolyols showed moderate activity against α‐ L ‐fucosidases and α‐ D ‐glucosidases, with K i values of 30−40 μ M .