Synthesis and biological characterization of new aryloxyindole-4,9-diones as potent trypanosomicidal agents

Ricardo A. Tapia, Cristian O. Salas, Karina Vázquez, Christian Espinosa-Bustos, Jorge Soto-Delgado, Javier Varela, Estefanía Birriel, Hugo Cerecetto, Mercedes González, Margot Paulino

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A new indole-4,9-dione and their phenoxy derivatives were synthesized and evaluated in vitro against the epimastigote form of Trypanosoma cruzi, Y strain. All of these novel compounds were found to be extremely potent and selective that the standard drug nifurtimox. Interestingly, phenoxyindole-4,9-dione 9d displayed excellent nanomolar inhibitory activity, IC50 = 20 nM, and high selectivity index, SI = 625. In silico studies using MOE program were performed to generate a preliminary pharmacophore model.

Original languageEnglish
Pages (from-to)3919-3922
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number16
DOIs
Publication statusPublished - 15 Aug 2014

Keywords

  • Anti-T. cruzi
  • Cytotoxicity
  • Indolequinones
  • Pharmacophore model

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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