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

José C. Aponte, Manuela Verástegui, Edith Málaga, Mirko Zimic, Miguel Quiliano, Abraham J. Vaisberg, Robert H. Gilman, Gerald B. Hammond

Research output: Contribution to journalArticle

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 μM, four of which exhibited a selectivity index greater than 12.

Original languageEnglish (US)
Pages (from-to)6230-6234
Number of pages5
JournalJournal of medicinal chemistry
Volume51
Issue number19
DOIs
StatePublished - Oct 9 2008

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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    Aponte, J. C., Verástegui, M., Málaga, E., Zimic, M., Quiliano, M., Vaisberg, A. J., Gilman, R. H., & Hammond, G. B. (2008). Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones. Journal of medicinal chemistry, 51(19), 6230-6234. https://doi.org/10.1021/jm800812k