Synthesis and evaluation of a 5-membered isoiminosugar as glycosidase inhibitor

Recent Developments of Transition-State Analogue Glycosidase Inhibitors of Non-Natural Product Origin

“…213 Among analogues of 1-azafagomine mainly the 3-position (carbohydrate numbering) has been explored. Interestingly, 3-deoxy-3-fluoro analogue 321 was a much poorer inhibitor than 1-azafagomine (118) itself. This suggests that the 3-OH of 1-azafagomine ( 118) is involved in hydrogen bonding.…”

“…Neither enantiomer had any significant activity, 116 which was also the case for iminosugar 160, which additionally was tested against galactosidases, mannosidases, xylosidases, and an R-L-fucosidase. 118 As a potential inhibitor of fucosidases, the analogue of 125 was prepared with the 5-methyl group ex- changed for a methyleno or a methoxy substituent.…”

A Practical Large-Scale Synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol via Asymmetric 1,3-Dipolar Cycloaddition

“…Racemic and nonracemic 4-(hydroxymethyl)pyrrolidin-3-ols have been prepared and found to have an inhibitory effect on certain enzymes [1][2][3] and on glial GABA uptake. 4 These pyrrolidines have also been used as building blocks for the synthesis of some compounds having antibacterial activity 5,6 and also for some nucleoside analogues.…”

“…Racemic and nonracemic 4-(hydroxymethyl)pyrrolidin-3-ols have been prepared and found to have an inhibitory effect on certain enzymes − and on glial GABA uptake , and also for some nucleoside analogues.…”

Σύνθεση Αλκαλοειδών Ως Πιθανών Αναστολέων Γλυκοζιτασών Από Φυσικά Χειρόμορφα Υποστρώματα

“…Με την μεθοδολογία αυτή έχει επιτευχθεί η σύνθεση της καστανοσπερμίνης, όπου σε ένα στάδιο γίνεται τριπλή αναγωγική αμινοκυκλοποίηση του παράγωγου της D-γλυκόζης 78 81. 21Η εισαγωγή της αμινο-ομάδας στο σκελετό σακχάρων μπορεί να επιτευχθεί με τη μορφή της νιτρο ή της κυανο-ομάδας 82,83. Επίδραση διαιθυλοκυανο-αργιλίου στο εποξείδιο 80 οδηγεί στο κυανο παράγωγο 81, το οποίο κυκλοποιείται αναγωγικά προς την πυρρολιδίνη 82.…”