3867-86-5Relevant articles and documents
Diastereoselective synthesis of glycopyrans 1,2-annulated with dioxazinanes from 1,2-anhydrosugars and N-substituted nitrones
Ahmed, Ajaz,Sakander, Norein,Rasool, Faheem,Hussain, Nazar,Mukherjee, Debaraj
, p. 1436 - 1443 (2022/02/25)
1,2-Annulated pyranose sugars fused with six membered rings have emerged as an important class of carbohydrates with wide biological and synthetic utility. We now describe zinc chloride catalyzed one pot diastereoselective synthesis of sugar fused dioxazinanes from 1,2-anhydro sugars and N-substituted aromatic nitrones. Various aromatic nitrones with different substituents undergo the reaction smoothly. The developed strategy works well with both ester and ether protection on the sugar and proceeds under mild reaction conditions. The mechanism seems to involve activation of the anhydrosugar by ZnCl2 for nucleophilic attack by the nitrone followed by cyclization.
β-Configured clickable [18F]FDGs as novel 18F-fluoroglycosylation tools for PET
Elgland,Nordeman,Fyrner,Antoni,Nilsson, K. Peter R.,Konradsson
supporting information, p. 10231 - 10236 (2017/09/18)
In oncology and neurology the 18F-radiolabeled glucose analogue 2-deoxy-2-[18F]fluoro-d-glucose ([18F]FDG) is by far the most commonly employed metabolic imaging agent for positron emission tomography (PET). Herein, we report a novel synthetic route to β-configured mannopyranoside precursors and a chemoselective 18F-fluoroglycosylation method that employ two β-configured [18F]FDG derivatives equipped with either a terminal azide or alkyne aglycon respectively, for use as a CuAAC clickable tool set for PET. The β-configured precursors provided the corresponding [18F]FDGs in a radiochemical yield of 77-88%. Further, the clickability of these [18F]FDGs was investigated by click coupling to the suitably functionalized Fmoc-protected amino acids, Fmoc-N-(propargyl)-glycine and Fmoc-3-azido-l-alanine, which provided the 18F-fluoroglycosylated amino acid conjugates in radiochemical yields of 75-83%. The 18F-fluoroglycosylated amino acids presented herein constitute a new and interesting class of metabolic PET radiotracers.
Conformationally-locked N -glycosides with selective β-glucosidase inhibitory activity: Identification of a new non-iminosugar-type pharmacological chaperone for gaucher disease
Castilla, Javier,Rísquez, Rocío,Cruz, Deysi,Higaki, Katsumi,Nanba, Eiji,Ohno, Kousaku,Suzuki, Yoshiyuki,Díaz, Yolanda,Mellet, Carmen Ortiz,Fernández, José M. García,Castillón, Sergio
supporting information; experimental part, p. 6857 - 6865 (2012/09/22)
A series of conformationally locked N-glycosides having a cis-1,2-fused pyranose-1,3-oxazoline-2-thione structure and bearing different substituents at the exocyclic sulfur has been prepared. The polyhydroxylated bicyclic system was built in only three steps by treatment of the corresponding readily available 1,2-anhydrosugar with KSCN using TiO(TFA)2 as catalyst, followed by S-alkylation and acetyl deprotection. In vitro screening against several glycosidase enzymes showed highly specific inhibition of mammalian β-glucosidase with a marked dependence of the potency upon the nature of the exocyclic substituent. The most potent representative, bearing an S-(ω-hydroxyhexadecyl) substituent, was further assayed as inhibitor of the human lysosomal β-glucocerebrosidase and as pharmacological chaperone in Gaucher disease fibroblasts. Activity enhancements in N370S/N370S mutants analogous to those achieved with the reference compound ambroxol were attained with a more favorable chaperone/inhibitor balance.
