Journal ArticleDOI
Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising Analogues
TLDR
It was shown that the difficultly accessible isopropylidene side chain of spirotryprostatin A is not necessary for biological activity and three analogues lacking the diketopiperazine system were shown to be quite active as cell cycle inhibitors.Abstract:
The total synthesis of the title compound has been accomplished. A key step involves the oxidative rearrangement of the β-carboline derivative to an oxindole via the action of N-bromosuccinimide. From this point, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidene function. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led to the parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain of spirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazine system were shown to be quite active as cell cycle inhibitors.read more
Citations
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Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.
TL;DR: The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties.
Journal ArticleDOI
Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids
TL;DR: The spiro[pyrrolidine-3,3′-oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis as discussed by the authors.
Journal ArticleDOI
2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.
Journal ArticleDOI
Recent Advances in Asymmetric Organocatalytic Construction of 3,3′-Spirocyclic Oxindoles
Liang Hong,Rui Wang,Rui Wang +2 more
TL;DR: Recent advances in asymmetric organocatalysis are summarized and classified according to the spiro ring fused at the 3-position of the oxindole core.
Journal ArticleDOI
Metal-catalyzed alpha-arylation of carbonyl and related molecules: novel trends in C-C bond formation by C-H bond functionalization.
TL;DR: This Review summarizes the developments in this area to date, with a focus on how the substrate scope has been expanded through selection of the most appropriate synthetic method, such as the careful choice of ligands, precatalysts, bases, and reaction conditions.
References
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Journal ArticleDOI
Tryprostatin A, a specific and novel inhibitor of microtubule assembly.
TL;DR: Results indicate that TPS-A is a novel inhibitor of MAP-dependent microtubules assembly and, through the disruption of the microtubule spindle, specifically inhibits cell cycle progression at the M phase.
Journal ArticleDOI
Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase☆
TL;DR: Spirotryprostatins A and B had a novel structural skeleton with an unique spiro ring system and inhibited the cell cycle progression of tsFT210 cells at the G2/M phase with IC50 values of 197.5 μM and 14.0 μM, respectively.
Journal ArticleDOI
Novel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus fumigatus I. Taxonomy, Fermentation, Isolation and Biological Properties
TL;DR: The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 microM and 12.2 microM, respectively.