Journal article

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

Brett D Schwartz, Mark J Coster, Tina S Skinner-Adams, Katherine T Andrews, Jonathan M White, Rohan A Davis

Marine Drugs | MDPI AG | Published : 2015

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 inhibiti..

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University of Melbourne Researchers

Grants

Awarded by National Health and Medical Research Council (NHMRC)


Awarded by Australian Research Council (ARC)


Awarded by ARC


Funding Acknowledgements

We thank the National Health and Medical Research Council (NHMRC) for financial support towards this research through a project grant (APP1024314). R.A.D. and K.T.A. acknowledge the Australian Research Council (ARC) for an ARC Linkage Grant (LP120200339) and an ARC Future Fellowship, respectively. We also thank the ARC for support toward NMR and MS equipment (Grant LE0668477 and LE0237908). G. MacFarlane (University of Queensland) and W. Loa (Griffith University) are acknowledged for HRESIMS measurements. We also acknowledge the Australian Red Cross Blood Service for the provision of human blood and sera.