Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A-D
AuthorSchwartz, BD; Coster, MJ; Skinner-Adams, TS; Andrews, KT; White, JM; Davis, RA
Source TitleMarine Drugs
University of Melbourne Author/sWhite, Jonathan
AffiliationSchool of Chemistry
Document TypeJournal Article
CitationsSchwartz, B. D., Coster, M. J., Skinner-Adams, T. S., Andrews, K. T., White, J. M. & Davis, R. A. (2015). Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A-D. MARINE DRUGS, 13 (9), pp.5784-5795. https://doi.org/10.3390/md13095784.
Access StatusOpen Access
ARC Grant codeARC/LE0775481
Six regioisomers associated with the tricyclic core of thiaplakortones A-D have been synthesized. Reaction of 1H-indole-4,7-dione and 1-tosyl-1H-indole-4,7-dione with 2-aminoethanesulfinic acid afforded a regioisomeric series, which was subsequently deprotected and oxidized to yield the tricyclic core scaffolds present in the thiaplakortones. All compounds were fully characterized using NMR and MS data. A single crystal X-ray structure was obtained on one of the N-tosyl derivatives. All compounds were screened for in vitro antiplasmodial activity against chloroquine-sensitive (3D7) and multidrug-resistant (Dd2) Plasmodium falciparum parasite lines. Several analogues displayed potent inhibition of P. falciparum growth (IC50 < 500 nM) but only moderate selectivity for P. falciparum versus human neonatal foreskin fibroblast cells.
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