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Search for "azasugars" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases
Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189
- target GMIIb enzyme. In contrast, no inhibition effect of the pyrrolidines against LManII was observed. The modification of the imino-L-lyxitol core is therefore a suitable motif for the design of inhibitors with desired selectivity against the target GMIIb enzyme. Keywords: azasugars; hydrolases
Exploring endoperoxides as a new entry for the synthesis of branched azasugars
Beilstein J. Org. Chem. 2017, 13, 644–647, doi:10.3762/bjoc.13.63
- + 2]-cycloaddition between a diene and singlet oxygen. The endoperoxides were dihydroxylated and protected to provide a series of endoperoxide building blocks for organic synthesis, with potential use as precursors for the synthesis of branched azasugars. Preliminary exploration of the chemistry of
- these building blocks provided access to a variety of derivatives including tetrahydrofurans, epoxides and protected amino-tetraols. Keywords: azasugar; carbohydrate; cycloaddition; endoperoxide; photochemistry; Introduction Azasugars are small organic compounds that can mimic carbohydrates or their
- azasugars, such as the natural product deoxynojirimycin, to inhibit the activity of a wide range of enzymes has attracted attention for their potential use as drug candidates [2][3]. Azasugars in clinical use today include Glyset, a licensed drug for treatment of diabetes type II, and Zavesca, which is used
Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes
Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184
- organic synthesis [15][16][17][18][19][20][21][22][23][24], applications of nitroso hetero-Diels–Alder reactions for the synthesis of azasugars [10], and the utilization of nitroso hetero-Diels–Alder reactions in natural product synthesis [9][25] and the synthesis of bioactive molecules [26]. However
Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar
Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282
- strategy for the synthesis of diversely functionalized trihydroxypiperidines through double reductive amination of the D-mannose-derived aldehyde 2 (Scheme 1) [24][25]. Among the 1-azasugars accessed with this methodology, our attention was drawn to the enantiomer of natural 3,4,5-trihydroxypiperidine (1
Stereoselectively fluorinated N-heterocycles: a brief survey
Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306
- as polyhydroxylated alkaloids or azasugars, are sugar mimics in which a nitrogen atom replaces the ring oxygen of the corresponding monosaccharide (Figure 8) [31][32][33][34][35][36]. Iminosugars can competitively bind to glycosidase enzymes because of their structural resemblance to the terminal
A new approach toward the total synthesis of (+)-batzellaside B
Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210
- . Undoubtedly, approval of Glyset [9] and Miglustat [10] (Figure 1) for treatment of type II diabetes and Gaucher disease, respectively, has imparted therapeutic applications of this class of natural products. In this context, (+)-batzellasides A–C (1a–c) (Figure 2), C-alkylated azasugars isolated in 2004 from
Metathesis access to monocyclic iminocyclitol-based therapeutic agents
Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81
- , Potchefstroom 2520, South Africa Macromolecular Chemistry and Organic Catalysis, Institute of Chemistry (B6a), University of Liège, Sart Tilman, Liège 4000, Belgium 10.3762/bjoc.7.81 Abstract By focusing on recent developments on natural and non-natural azasugars (iminocyclitols), this review bolsters the case
- improvements brought about by introduction of one or more metathesis steps are outlined, with emphasis on the exquisite steric control and atom-economical outcome of the overall process. The comparative performance of several established metathesis catalysts is also highlighted. Keywords: azasugars
- ; iminocyclitols; natural products; olefin metathesis; Ru-alkylidene catalysts; Review Introduction Synthetic and natural polyhydroxylated N-heterocyclic compounds (pyrrolidines, piperidines, piperazines, indolizines, etc., and higher homologues), commonly referred to as azasugars, iminosugars or iminocyclitols
Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds
Beilstein J. Org. Chem. 2007, 3, No. 48, doi:10.1186/1860-5397-3-48
- . Background Azabicyclo [x.y.0]alkane scaffolds are ubiquitous structural elements in pharmaceutically important peptide mimetics [1][2][3] and several important classes of natural products such as indolizidine and quinolizidine alkaloids and azasugars. [4][5][6] In consequence, a number of groups have
A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine
Beilstein J. Org. Chem. 2007, 3, No. 41, doi:10.1186/1860-5397-3-41
- ,[11] and photomechanical biomaterials etc.[12] On the other hand, hydroxylated indolizidines [13][14][15][16][17][18][19][20] such as castanospermine, (−)-swainsonine, (+)-lentiginosine (1) [21][22][23] and (−)-2-epilentiginosine (2) [21][22][23][24][25][26] constitute a class of azasugars showing
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