Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones

  • J Med Chem. 2008 Oct 9;51(19):6230-4. doi: 10.1021/jm800812k.
José C Aponte  1 ,  Manuela Verástegui ,  Edith Málaga ,  Mirko Zimic ,  Miguel Quiliano ,  Abraham J Vaisberg ,  Robert H Gilman ,  Gerald B Hammond
Affiliations
  • 1. Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.
PMID: 18798609 DOI: 10.1021/jm800812k
Abstract

Synthesis of a cytotoxic dihydrochalcone, first isolated from a traditional Amazonian medicinal plant Iryanthera juruensis Warb (Myristicaceae), followed by a comprehensive SAR analysis of saturated and unsaturated chalcone synthetic intermediates, led to the identification of analogues with selective and significant in vitro anti- Trypanosoma cruzi activity. Further SAR studies were undertaken with the synthesis of 21 new Chalcones containing two allyloxy moieties that resulted in the discovery of 2',4'-diallyloxy-6'-methoxy Chalcones with improved selectivity against this Parasite at concentrations below 25 microM, four of which exhibited a selectivity index greater than 12.

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