Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A–D
| Autor: | Brett D. Schwartz, Mark J. Coster, Tina S. Skinner-Adams, Katherine T. Andrews, Jonathan M. White, Rohan A. Davis |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | Marine Drugs, Vol 13, Iss 9, Pp 5784-5795 (2015) |
| Druh dokumentu: | article |
| ISSN: | 1660-3397 64374599 |
| DOI: | 10.3390/md13095784 |
| Popis: | 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. |
| Databáze: | Directory of Open Access Journals |
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