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Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20
Graphical Abstract
Scheme 1: Biologically active compounds with a spirobarbiturate moiety in their structure [7-12].
Scheme 2: Biologically active alkaloids with a pyrrolizidine moiety.
Scheme 3: Previous studies on the three-component synthesis of spirobarbiturates.
Scheme 4: Synthesis of racemic spirobarbiturates 4a–p via one-pot three-component reaction of alloxan (1), ʟ-...
Scheme 5: A plausible mechanism of spirobarbiturate formation from alloxan (1), ʟ-proline (2), and N-substitu...
Figure 1: Schematic structures of endo- and exo-adducts of spirobarbiturates 4.
Figure 2: X-ray crystal structures of compounds 4b (CCDC 2391172, left) and 4c (CCDC 2391171, right).
Figure 3: Unit cell packing of products 4b (left) and 4c (right).
Figure 4: HS mapped with dnorm for compounds 4b (left) and 4c (right).
Figure 5: A segment of the crystal structure of compound 4b with the HS (dnorm), showing intermolecular conta...
Figure 6: A segment of the crystal structure of compound 4c with the HS (dnorm), showing intermolecular conta...
Figure 7: Microscopic images of treated cells and state of the actin cytoskeleton of Sk-mel-2 cells after cul...
Figure 8: Docked view of compounds 4f, 4g, 4i, 4k, and 4l with the target protein (PDB ID: 8DNH).