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Beilstein J. Org. Chem. 2013, 9, 2916–2924, doi:10.3762/bjoc.9.328
Graphical Abstract
Figure 1: Binding affinities of salvinorin A (1) and furan derivatives for κ-OR [5].
Figure 2: Crystal structure of κ-OR in complex with JDTic compared to naltrindole’s binding pose in δ-OR. A: ...
Figure 3: Previously reported N-furanylalkyl opioid antagonists [19,20].
Scheme 1: Syntheses of heteromethylated derivatives of 1. b.r.s.m. = based on recovered starting material.
Scheme 2: Synthesis of (2-hydroxyethoxy)methyl ether 6.
Figure 4: Crystal structure of 2 with 50% probability thermal displacement ellipsoids (cross-eyed stereoview)...
Figure 5: Key 1H–13C HMBC correlations.
Figure 6: Known low-affinity derivatives of 1 screened in addition to 2–5 for negative allosteric modulation ...
Beilstein J. Org. Chem. 2007, 3, No. 1, doi:10.1186/1860-5397-3-1
Figure 1: Stereoview of the molecular structure of 2b, showing 50% probability displacement ellipsoids and th...
Figure 2: Stereoview of the packing of 2b. H atoms are not shown.
Scheme 1: Koreeda et al's proposed mechanism for the epimerization.