Stable analogues of nojirimycin--synthesis and biological evaluation of nojiristegine and manno-nojiristegine.
Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark. hhj@chem.au.dk.
Agnete H
AH
Viuff
Louise M
LM
Besenbacher
Akiko
A
Kamori
Mikkel T
MT
Jensen
Mogens
M
Kilian
Atsushi
A
Kato
Henrik H
HH
Jensen
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004355:Drug Stability; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008358:Mannose / Q000737:chemistry*; D000520:alpha-Glucosidases / Q000378:metabolism
D000900:Anti-Bacterial Agents; D065089:Glycoside Hydrolase Inhibitors; D017485:1-Deoxynojirimycin; D000520:alpha-Glucosidases; D008358:Mannose; C013626:nojirimycin