| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349856 | Tetrahedron: Asymmetry | 2009 | 11 Pages |
Four dimeric and four monomeric lipophilic iminosugars were synthesized and subsequently evaluated on their inhibitory potential towards mammalian glucosylceramide synthase, glucocerebrosidase, β-glucosidase 2, sucrase and lysosomal α-glucosidase. Compared to their monomeric counterparts the dimeric inhibitors showed decreased inhibition of glucosylceramide synthase and generally a comparable inhibitory potency for the glycosidases.
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N,N′-{5,5′-[2-(Adamantan-1-yl)propane-1,3-diyl]bis(oxy)bis(pentane-5,1-diyl)}-bis(2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin)C91H112N2O10[α]D20=-2.4 (c 3.7 CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5R)
N,N′-{5,5′-[2-(Adamantan-1-yl)propane-1,3-diyl]bis(oxy)bis(pentane-5,1-diyl)}-bis(2,3,4,6-tetra-O-benzyl-l-ido-1-deoxynojirimycin)C91H112N2O10[α]D20=-21.8 (c 1.8 CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
N,N′-{5,5′-[Adamantan-1,3-diylbis(methylene)]bis(oxy)bis(pentane-5,1-diyl)}-bis(2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin)C90H110N2O10[α]D20=-3.0 (c 2.4 CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5R)
N,N′-{5,5′-[Adamantan-1,3-diylbis(methylene)]bis(oxy)bis(pentane-5,1-diyl)}-bis(2,3,4,6-tetra-O-benzyl-l-ido-1-deoxynojirimycin)C90H110N2O10[α]D20=-25.9 (c 2.1 CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
N,N′-{5,5′-[2-(Adamantan-1-yl)propane-1,3-diyl]bis(oxy)bis(pentane-5,1-diyl)}-bis(1-deoxynojirimycin)C35H64N2O10[α]D20=-8.8 (c 1.9 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5R)
N,N′-{5,5′-[2-(Adamantan-1-yl)propane-1,3-diyl]bis(oxy)bis(pentane-5,1-diyl)}-bis(l-ido-1-deoxynojirimycin)C35H64N2O10[α]D20=+11.4 (c 2.6 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
N,N′-{5,5′-[Adamantan-1,3-diylbis(methylene)]bis(oxy)bis(pentane-5,1-diyl)}-bis(1-deoxynojirimycin)C34H62N2O10[α]D20=-3.6 (c 3.6 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5R)
N,N′-{5,5′-[Adamantan-1,3-diylbis(methylene)]bis(oxy)bis(pentane-5,1-diyl)}-bis(l-ido-1-deoxynojirimycin)C34H62N2O10[α]D20=+13.2 (c 3.1 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
N-[5-(Adamantan-1-yl-ethoxy)-pentyl]-1-deoxynojirimycinC23H41NO5[α]D20=-16.6 (c 0.8 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5R)
N-[5-(Adamantan-1-yl-ethoxy)-pentyl]-l-ido-1-deoxynojirimycinC23H41NO5[α]D20=+11.9 (c 0.8 MeOH)Source of chirality: d-glucoseAbsolute configuration: (2S,3R,4R,5S)
