The unexpected rearrangement of 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-one products of the tandem Ugi 4CC/intramolecular Diels-Alder reaction in 85% H3PO4 was discovered to provide diastereomerically pure tricyclic bislactam lactone-containing natural product-like products in high yield. Mechanistic rationale for the observed rearrangement was proposed and has been tentatively confirmed by additional experiments.

From the authors'650,000 compound collection, they have selected approximately 15,000 potential small-molecule protease inhibitors, which were subjected to high-throughput screening against caspase-3. The screening yielded a series of hits that belong to 11 different scaffolds. Based on the structure of one of the hits, a new class of the small-molecule inhibitors with a double electrophilic warhead, 8-sulfonyl-pyrrolo[3,4-c]quinoline-1,3-diones (SPQ), was synthesized and tested in follow-up mechanistic and antiapoptosis assays. Mechanistic analysis of a representative compound of this class, CD-001-0011, showed that the compound exhibited a high potency (IC 50 = 130 nM), was reversible though noncompetitive, and had a broad selectivity profile to other caspases belonging to groups I to III. The compound was effective in preventing staurosporineinduced apoptosis in a few cell lines and retinoic acid-induced apoptosis in zebrafish. (Journal of Biomolecular Screening 2006:277-285)

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Starting from 5-sulfamoylisatins, 6-sulfamoyl-4-quinolinecarboxylic acids and 2-methyl-6-sulfamoylquinoline-3,4-dicarboxylic acids were prepared by the Pfitzinger reaction. These acids and diacids were then converted to the corresponding amide and imide libraries. A patent based on these new combinatorial chemical libraries has been applied for. All the newly synthesized compounds are crystalline substances that were purified by recrystallization from suitable solvents and characterized primarily by 1H NMR, 13C NMR, and mass spectrometry.