Antimalarial activity of 10-alkyl/aryl esters and -aminoethylethers of artemisinin

Theunis T. Cloete, Henk J. Krebs, Julie A. Clark, Michele C. Connelly, Amy Orcutt, Martina S. Sigal, R. Kiplin Guy, David D. N'Da

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


A series of n-alkyl/aryl esters were synthesized and their in vitro antiplasmodial activity was measured alongside that of previously synthesized aminoethylethers of artemisinin ozonides against various strains of Plasmodium falciparum. The cytotoxicity against human cell lines was also assessed. The esters were synthesized in a one-step reaction by derivatization on carbon C-10 of dihydroartemisinin. Both classes were active against both the 3D7 and K1 strains of P. falciparum, with all compounds being significantly more potent than artemether against both strains. The majority of compounds possessed potency either comparable or more than artesunate with a high degree of selectivity towards the parasitic cells. The 10α-n-propyl 11 and 10α-benzyl 18 esters were the most potent of all synthesized ozonides, possessing a moderate (∼3-fold) and significant (22- and 12-fold, respectively) potency increases against the 3D7 and K1 strains, respectively, in comparison with artesunate.

Original languageEnglish
Pages (from-to)10-16
Number of pages7
JournalBioorganic Chemistry
Issue number1
StatePublished - Feb 2013

Bibliographical note

Funding Information:
The authors thank the National Research Foundation (NRF) and the North-West University (NWU) for financial support.


  • Artemether
  • Artesunate
  • Cytotoxicity
  • Ozonide
  • Plasmodium falciparum

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry


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