New chemical and biological aspects of artemisinin-derived trioxane dimers

Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. H-1 NMR spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dinners 5a and 5b, are promising for chemotherapy of both malaria and cancer. (C) 2001 Elsevier Science Ltd. All rights reserved.