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Article

Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A–D

1
Eskitis Institute for Drug Discovery, Griffith University, Nathan, Qld 4111, Australia
2
School of Chemistry and Bio21 Institute, University of Melbourne, Parkville, Vic 3052, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Sylvia Urban
Mar. Drugs 2015, 13(9), 5784-5795; https://doi.org/10.3390/md13095784
Received: 14 August 2015 / Revised: 4 September 2015 / Accepted: 7 September 2015 / Published: 15 September 2015
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. View Full-Text
Keywords: synthesis; thiaplakortone; regioisomer; tricyclic; natural product scaffold; X-ray; crystal; Plasmodium falciparum; antiplasmodial; cytotoxicity synthesis; thiaplakortone; regioisomer; tricyclic; natural product scaffold; X-ray; crystal; Plasmodium falciparum; antiplasmodial; cytotoxicity
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MDPI and ACS Style

Schwartz, B.D.; Coster, M.J.; Skinner-Adams, T.S.; Andrews, K.T.; White, J.M.; Davis, R.A. Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A–D. Mar. Drugs 2015, 13, 5784-5795. https://doi.org/10.3390/md13095784

AMA Style

Schwartz BD, Coster MJ, Skinner-Adams TS, Andrews KT, White JM, Davis RA. Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A–D. Marine Drugs. 2015; 13(9):5784-5795. https://doi.org/10.3390/md13095784

Chicago/Turabian Style

Schwartz, Brett D., Mark J. Coster, Tina S. Skinner-Adams, Katherine T. Andrews, Jonathan M. White, and Rohan A. Davis 2015. "Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A–D" Marine Drugs 13, no. 9: 5784-5795. https://doi.org/10.3390/md13095784

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