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Mar. Drugs 2015, 13(9), 5784-5795; doi:10.3390/md13095784

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
Received: 14 August 2015 / Revised: 4 September 2015 / Accepted: 7 September 2015 / Published: 15 September 2015
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Abstract

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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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