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Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175
Graphical Abstract
Figure 1: Lactosylthioureidocalix[4]arenes I–III used to inhibit Gal-3 [20,21].
Figure 2: The new glycocalix[4]arenes 1–4 synthesized in this study.
Scheme 1: Synthesis of the cone galactosylcalix[4]arenes 1. Reaction conditions: (i) DCC, DMAP, CH2Cl2, under...
Scheme 2: Synthesis of the cone galactosylcalix[4]arenes 2. Reaction conditions: (i) DIPEA, CH2Cl2, rt, 6 h, ...
Scheme 3: Synthesis of the cone lactosylcalix[4]arenes 3. Reaction conditions: (i) NaN3, n-Bu4NI, DMF, 90 °C,...
Scheme 4: Synthesis of the 1,3-alternate lactosylcalix[4]arenes 4. Reaction conditions: (i) EDC, CH2Cl2/py (7...
Figure 3: SPR sensorgrams of binding experiment between immobilized Gal-3 and glycocalixarenes 1, 3 and 4.
Figure 4: a) Relative affinities of glycocalixarene 1, 3, 4 (1 mM) towards Gal-3, expressed in terms of the i...